JP7389059B2 - Substituted phenylpyrimidines with herbicidal activity - Google Patents

Description

The present invention relates to the technical field of herbicides, in particular for the selective control of weeds and grasses in crops of useful plants.

In particular, the present invention relates to substituted phenylpyrimidines, methods of their preparation, and their use as herbicides.

WO 2016/120355 describes substituted phenylpyrimidines with a carbonyl group directly attached to the 4-position of the pyrimidine. WO 2018/019555 describes substituted phenylpyrimidine carboxylic acid derivatives with an extended side chain in the 4-position. The herbicidal activity of these known compounds, especially at low application rates, and/or their compatibility with crop plants remains in need of improvement.

For the reasons stated, there remains a need for potent herbicides and/or plant growth regulators for selective use in crop plants or for use in non-agricultural areas, and these active ingredients are preferably , should have additional advantageous properties in application, such as improved compatibility with crop plants.

International Publication No. 2016/120355 International Publication No. 2018/019555

Therefore, even relatively low application rates are highly effective against economically important harmful plants and can be used selectively in crop plants, preferably with good activity against harmful plants, and at the same time It is an object of the present invention to provide compounds (herbicides) with herbicidal activity, preferably having good compatibility with crop plants. Preferably, these herbicidal compounds should be particularly effective and efficient against a wide range of weedy grasses and preferably also have good activity against a large number of weeds.

It has now been found that the following compounds of formula (I) and their salts have excellent herbicidal activity against a wide range of economically important monocotyledonous and dicotyledonous annual harmful plants.

（式中、記号および指数は以下の意味を有する：
Xは、C（R¹³）（R¹⁴）を表し、
R¹は、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニルまたはヘテロシクリルを表し、ここで、これらの3つの上記基は、各々、ハロゲン、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₂～C₆）－アルケニル、ハロ－（C₂～C₆）－アルケニル、（C₂～C₆）－アルキニル、ハロ－（C₃～C₆）－アルキニル、（C₃～C₆）－シクロアルキル、ハロ－（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、ハロ－（C₃～C₆）－シクロアルケニル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルケニル－（C₁～C₆）－アルキル、ハロ－（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、ハロ－（C₃～C₆）－シクロアルケニル－（C₁～C₆）－アルキル、R⁸（O）C、R⁸O（O）C、（R⁸）₂N（O）C、R⁸O、（R⁸）₂N、R⁹（O）_nS、フェニル、ヘテロアリール、ヘテロシクリル、フェニル－（C₁～C₆）－アルキル、ヘテロアリール－（C₁～C₆）－アルキルおよびヘテロシクリル－（C₁～C₆）－アルキルからなる群のs個の基により置換されており、ここで、これらの後の6つの基は、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₁～C₆）－アルコキシ、ハロ－（C₁～C₆）－アルコキシおよびハロゲンからなる群のm個の基によって置換されており、シクロアルキル、シクロアルケニルおよびヘテロシクリルは、各々独立にn個のオキソ基を有し、
R²は、ヒドロキシ、（C₁～C₆）－アルコキシ、（C₂～C₆）－アルケニルオキシ、（C₂～C₆）－アルキニルオキシ、（C₁～C₆）－ハロアルコキシ、（C₂～C₆）－ハロアルケニルオキシ、（C₂～C₆）－ハロアルキニルオキシを表し、ここで、これらの後の6つの基は、各々、シアノ、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、ハロ－（C₃～C₆）－シクロアルキル、ハロ－（C₃～C₆）－シクロアルケニル、R⁸（O）C、R⁸（R⁸ON＝）C、R⁸O（O）C、R⁹S（O）C、（R⁸）₂N（O）C、R⁸（R⁸O）N（O）C、（R⁸）₂N（R⁸）N（O）C、R⁸（O）C（R⁸）N（O）C、R⁹O（O）C（R⁸）N（O）C、（R⁸）₂N（O）C（R⁸）N（O）C、R⁹（O）₂S（R⁸）N（O）C、R⁸O（O）₂S（R⁸）N（O）C、（R⁸）₂N（O）₂S（R⁸）N（O）C、R⁸O、R⁸（O）CO、R⁹（O）₂SO、R⁹O（O）CO、（R⁸）₂N（O）CO、（R⁸）₂N、R⁸（O）C（R⁸）N、R⁹（O）₂S（R⁸）N、R⁹O（O）C（R⁸）N、（R⁸）₂N（O）C（R⁸）N、R⁸O（O）₂S（R⁸）N、（R⁸）₂N（O）₂S（R⁸）N、R⁹（O）_nS、R⁸O（O）₂S、（R⁸）₂N（O）₂S、R⁸（O）C（R⁸）N（O）₂S、R⁹O（O）C（R⁸）N（O）₂S、（R⁸）₂N（O）C（R⁸）N（O）₂S、R¹¹ ₃Si、（R¹²O）₂（O）P、フェニル、ヘテロアリールおよびヘテロシクリルからなる群のs個の基により置換されており、ここで、これらの後の3つの基は、各々、ニトロ、ハロゲン、シアノ、チオシアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルからなる群のm個の基により置換されているか、
または
R²は、（C₃～C₆）－シクロアルコキシ、（C₃～C₆）－シクロアルケニルオキシ、フェニルオキシ、ヘテロアリールオキシまたはヘテロシクリルオキシを表し、これらの5つの上記基は、各々、ハロゲン、シアノ、（C₁～C₆）－アルキル、（C₂～C₆）－アルケニル、（C₂～C₆）－アルキニル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、ハロ－（C₃～C₆）－シクロアルキル、ハロ－（C₃～C₆）－シクロアルケニル、R⁸（O）C、R⁸（R⁸ON＝）C、R⁸O（O）C、R⁹S（O）C、（R⁸）₂N（O）C、R⁸（R⁸O）N（O）C、（R⁸）₂N（R⁸）N（O）C、R⁸（O）C（R⁸）N（O）C、R⁹O（O）C（R⁸）N（O）C、（R⁸）₂N（O）C（R⁸）N（O）C、R⁹（O）₂S（R⁸）N（O）C、R⁸O（O）₂S（R⁸）N（O）C、（R⁸）₂N（O）₂S（R⁸）N（O）C、R⁸O、R⁸（O）CO、R⁹（O）₂SO、R⁹O（O）CO、（R⁸）₂N（O）CO、（R⁸）₂N、R⁸（O）C（R⁸）N、R⁹（O）₂S（R⁸）N、R⁹O（O）C（R⁸）N、（R⁸）₂N（O）C（R⁸）N、R⁸O（O）₂S（R⁸）N、（R⁸）₂N（O）₂S（R⁸）N、R⁹（O）_nS、R⁸O（O）₂S、（R⁸）₂N（O）₂S、R⁸（O）C（R⁸）N（O）₂S、R⁹O（O）C（R⁸）N（O）₂S、（R⁸）₂N（O）C（R⁸）N（O）₂S、R₃ ¹¹Si、（R¹²O）₂（O）P、フェニル、ヘテロアリールおよびヘテロシクリルからなる群のs個の基により置換されており、ここで、これらの後の3つの基は、各々、ニトロ、ハロゲン、シアノ、チオシアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルからなる群のm個の基により置換されており、ここで（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、ヘテロシクリル、（C₃～C₆）－シクロアルコキシ、（C₃～C₆）－シクロアルケニルオキシおよびヘテロシクリルオキシは、各々独立に、n個のオキソ基を有するか、または
R²は、R⁸（O）CO、R⁹（O）₂SOまたはR¹⁵R¹⁶C＝N－Oまたは（R⁸）₂N－Oを表すか、
または
R²は、（R⁸）₂N、R⁸（O）C（R⁸）N、R⁹O（O）C（R⁸）N、（R⁸）₂N（O）C（R⁸）N、R⁹（O）₂S（R⁸）N、R⁸O（O）₂S（R⁸）N、（R⁸）₂N（O）₂S（R⁸）Nを表すか、
または
R²は、R⁸（R⁸O）Nを表すか
または
R²は、（R¹⁷）（R¹⁸）N（R¹⁹）Nを表すか、
または
R²は、R¹⁷R¹⁸C＝N－（R¹⁹）N－を表し
R³、R⁴、R⁵、R⁶およびR⁷は、各々独立に、水素、ニトロ、ハロゲン、シアノ、チオシアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₂～C₆）－アルケニル、ハロ－（C₂～C₆）－アルケニル、（C₂～C₆）－アルキニル、ハロ－（C₃～C₆）－アルキニル、（C₃～C₆）－シクロアルキル、ハロ－（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、ハロ－（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、R⁸（O）C、R⁸（R⁸ON＝）C、R⁸O（O）C、（R⁸）₂N（O）C、R⁸（R⁸O）N（O）C、（R⁸）₂N（R⁸）N（O）C、R⁸（O）C（R⁸）N（O）C、R⁹O（O）C（R⁸）N（O）C、（R⁸）₂N（O）C（R⁸）N（O）C、R⁹（O）₂S（R⁸）N（O）C、R⁸O（O）₂S（R⁸）N（O）C、（R⁸）₂N（O）₂S（R⁸）N（O）C、R⁸O、R⁸（O）CO、R⁹（O）₂SO、R⁹O（O）CO、（R⁸）₂N（O）CO、（R⁸）₂N、R⁸（O）C（R⁸）N、R⁹（O）₂S（R⁸）N、R⁹O（O）C（R⁸）N、（R⁸）₂N（O）C（R⁸）N、R⁸O（O）₂S（R⁸）N、（R⁸）₂N（O）₂S（R⁸）N、R⁹（O）_nS、R⁸O（O）₂S、（R⁸）₂N（O）₂S、R⁸（O）C（R⁸）N（O）₂S、R⁹O（O）C（R⁸）N（O）₂S、（R⁸）₂N（O）C（R⁸）N（O）₂S、（R¹²O）₂（O）P、R⁸（O）C－（C₁～C₆）－アルキル、R⁸O（O）C－（C₁～C₆）－アルキル、（R⁸）₂N（O）C－（C₁～C₆）－アルキル、（R⁸O）（R⁸）N（O）C－（C₁～C₆）－アルキル、（R⁸）₂N（R⁸）N（O）C－（C₁～C₆）－アルキル、R⁸（O）C（R⁸）N（O）C－（C₁～C₆）－アルキル、R⁹O（O）C（R⁸）N（O）C－（C₁～C₆）－アルキル、（R⁸）₂N（O）C（R⁸）N（O）C－（C₁～C₆）－アルキル、R⁹（O）₂S（R⁸）N（O）C－（C₁～C₆）－アルキル、R⁸O（O）₂S（R⁸）N（O）C－（C₁～C₆）－アルキル、（R⁸）₂N（O）₂S（R⁸）N（O）C－（C₁～C₆）－アルキル、NC－（C₁～C₆）－アルキル、R⁸O－（C₁～C₆）－アルキル、R⁸（O）CO－（C₁～C₆）－アルキル、R⁹（O）₂SO－（C₁～C₆）－アルキル、R⁹O（O）CO－（C₁～C₆）－アルキル、（R⁸）₂N（O）CO－（C₁～C₆）－アルキル、（R⁸）₂N－（C₁～C₆）－アルキル、R⁸（O）C（R⁸）N－（C₁～C₆）－アルキル、R⁹（O）₂S（R⁸）N－（C₁～C₆）－アルキル、R⁹O（O）C（R⁸）N－（C₁～C₆）－アルキル、（R⁸）₂N（O）C（R⁸）N－（C₁～C₆）－アルキル、R⁸O（O）₂S（R⁸）N－（C₁～C₆）－アルキル、（R⁸）₂N（O）₂S（R⁸）N－（C₁～C₆）－アルキル、R⁹（O）_nS－（C₁～C₆）－アルキル、R⁸O（O）₂S－（C₁～C₆）－アルキル、（R⁸）₂N（O）₂S－（C₁～C₆）－アルキル、R⁸（O）C（R⁸）N（O）₂S－（C₁～C₆）－アルキル、R⁹O（O）C（R⁸）N（O）₂S－（C₁～C₆）－アルキル、（R⁸）₂N（O）C（R⁸）N（O）₂S－（C₁～C₆）－アルキル、（R¹²O）₂（O）P－（C₁～C₆）－アルキル、フェニル、ヘテロアリール、ヘテロシクリル、フェニル－（C₁～C₆）－アルキル、ヘテロアリール－（C₁～C₆）－アルキルまたはヘテロシクリル－（C₁～C₆）－アルキルを表し、ここで、これらの後の6つの基は、各々ニトロ、ハロゲン、シアノ、チオシアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、R⁸O（O）C、（R⁸）₂N（O）C、R⁸O、（R⁸）₂N、R⁹（O）_nS、R⁸O（O）₂S、（R⁸）₂N（O）₂SおよびR⁸O－（C₁～C₆）－アルキルからなる群のm個の基によって置換されており、ここでシクロアルキルおよびヘテロシクリルは、各々独立にn個のオキソ基を有し、
R⁸は、水素、（C₁～C₆）－アルキル、（C₂～C₆）－アルケニル、（C₂～C₆）－アルキニル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルケニル－（C₁～C₆）－アルキル、（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルケニル－（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキルまたは（C₁～C₆）－アルキルチオ－（C₁～C₆）－アルキルを表し、ここで、これらの後の12の基はs個のハロゲン原子を有するか、
または
R⁸は、フェニル、フェニル－（C₁～C₆）－アルキル、ヘテロアリール、ヘテロアリール－（C₁～C₆）－アルキル、ヘテロシクリル、ヘテロシクリル－（C₁～C₆）－アルキル、フェニル－O－（C₁～C₆）－アルキル、ヘテロアリール－O－（C₁～C₆）－アルキル、ヘテロシクリル－O－（C₁～C₆）－アルキル、フェニル－N（R¹⁰）－（C₁～C₆）－アルキル、ヘテロアリール－N（R¹⁰）－（C₁～C₆）－アルキル、ヘテロシクリル－N（R¹⁰）－（C₁～C₆）－アルキル、フェニル－S（O）_n－（C₁～C₆）－アルキル、ヘテロアリール－S（O）_n－（C₁～C₆）－アルキルまたはヘテロシクリル－S（O）_n－（C₁～C₆）－アルキルを表し、ここで、基は、各々、ニトロ、ハロゲン、シアノ、チオシアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルからなる群のm個の基によって置換されており、
かつ（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニルおよびヘテロシクリルは、各々独立にn個のオキソ基を有するか、
または
R⁸基は、それらが結合している1個または複数のヘテロ原子と環、具体的にはヘテロシクリル、ヘテロシクレニル、ヘテロアリール、アリールヘテロシクリル、アリールヘテロシクレニル、ヘテロアリールヘテロシクリル、ヘテロアリールヘテロシクレニル、ヘテロシクリルヘテロアリールまたはヘテロシクレニルヘテロアリールを形成し、ここで、これらの環の各々は、今度はニトロ、ハロゲン、シアノ、チオシアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルおよびオキソからなる群のm個の基によって置換されており、
R⁹は、（C₁～C₆）－アルキル、（C₂～C₆）－アルケニル、（C₂～C₆）－アルキニル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルケニル－（C₁～C₆）－アルキル、（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルケニル－（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキルまたは（C₁～C₆）－アルキルチオ－（C₁～C₆）－アルキルを表し、ここで、基は、s個のハロゲン原子を有するか、
または
R⁹は、フェニル、フェニル－（C₁～C₆）－アルキル、ヘテロアリール、ヘテロアリール－（C₁～C₆）－アルキル、ヘテロシクリル、ヘテロシクリル－（C₁～C₆）－アルキル、フェニル－O－（C₁～C₆）－アルキル、ヘテロアリール－O－（C₁～C₆）－アルキル、ヘテロシクリル－O－（C₁～C₆）－アルキル、フェニル－N（R¹⁰）－（C₁～C₆）－アルキル、ヘテロアリール－N（R¹⁰）－（C₁～C₆）－アルキル、ヘテロシクリル－N（R¹⁰）－（C₁～C₆）－アルキル、フェニル－S（O）_n－（C₁～C₆）－アルキル、ヘテロアリール－S（O）_n－（C₁～C₆）－アルキルまたはヘテロシクリル－S（O）_n－（C₁～C₆）－アルキルを表し、ここで、基は、各々、ニトロ、ハロゲン、シアノ、チオシアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルからなる群のm個の基によって置換されており、
かつ（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニルおよびヘテロシクリルは、各々独立にn個のオキソ基を有し、
R¹⁰は、水素、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₂～C₆）－アルケニル、（C₂～C₆）－アルキニル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキルまたはフェニルを表し、
R¹¹は、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₂～C₆）－アルケニル、（C₂～C₆）－アルキニル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキルまたはフェニルを表し、
R¹²は、水素または（C₁～C₄）－アルキルを表し、
R¹³およびR¹⁴は、各々独立に、水素、（C₁～C₆）－アルキル、ヒドロキシ、（C₁～C₆）－アルコキシ、（R⁸）₂N、ハロ－（C₁～C₆）－アルコキシ、ハロゲン、ハロ－（C₁～C₆）－アルキル、シアノ、R⁸O（O）Cまたは（R⁸）₂N（O）Cを表すか、
または
R¹³およびR¹⁴は、それらが結合している炭素原子とともに（C₃～C₈）－シクロアルキル基を形成し、
R¹⁵およびR¹⁶は、各々独立に、（C₁～C₆）－アルキル、フェニル、（C₃～C₆）－シクロアルキル、ヘテロアリールまたはヘテロシクリルを表し、
R¹⁷およびR¹⁸およびR¹⁹は、独立に、R⁸またはR⁹S（O）₂、（R⁸）₂NS（O）₂、R⁸OS（O）₂、R⁹C（O）、（R⁸）₂NC（O）、（R⁸）₂NC（S）、R⁸OC（O）、R⁸OC（O）C（O）、（R⁸）₂NC（O）C（O）を表すか、
または（R¹⁷およびR¹⁸）または（R¹⁷およびR¹⁹）基は、それらが結合している1個または複数のヘテロ原子と環、具体的にはヘテロシクリル、ヘテロシクレニル、ヘテロアリール、アリールヘテロシクリル、アリールヘテロシクレニル、ヘテロアリールヘテロシクリル、ヘテロアリールヘテロシクレニル、ヘテロシクリルヘテロアリールまたはヘテロシクレニルヘテロアリールを形成し、ここで、これらの環の各々は、今度はニトロ、ハロゲン、シアノ、チオシアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルおよびオキソからなる群のm個の基によって置換されており、
mは、0、1、2、3、4または5を表し、
nは、0、1または2を表し、
sは、0、1、2、3、4、5、6、7、8、9、10または11を表す）
およびその農薬上許容される塩を提供する。 Compound of general formula (I)

(wherein the symbols and exponents have the following meanings:
X represents C(R ¹³ )(R ¹⁴ ),
R ¹ represents (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl or heterocyclyl, where these three above groups are respectively halogen, (C ₁ -C ₆ ) -Alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, halo-(C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, halo -(C ₃ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, halo-(C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, halo-(C ₃ - _C6 )-cycloalkenyl, ( _C3 - _C6 )-cycloalkyl-( _C1 - _{C6)-alkyl, (C3-C6 ) -cycloalkenyl-} ( _C1 - _C6 )-alkyl , halo-(C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, halo-(C ₃ -C ₆ )-cycloalkenyl-(C ₁ -C ₆ )-alkyl, R ⁸ ( O)C, ^R8O (O)C, ( ^R8 ) _2N (O)C, ^R8O , ( ^R8 ) _2N , ^R9 (O) _nS , phenyl, heteroaryl, heterocyclyl, phenyl substituted by s groups of the group consisting of -(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl and heterocyclyl-(C ₁ -C ₆ )-alkyl, where and these later six groups are (C ₁ -C ₆ )-alkyl, halo-(C 1 -C 6 )-alkyl, (C ₁ -C ₆ )-alkoxy, halo-(C ₁ -C ₆ )-alkyl, (C ₁ -C 6 )-alkyl, ₆ )-substituted by m groups of the group consisting of alkoxy and halogen, cycloalkyl, cycloalkenyl and heterocyclyl each independently having n oxo groups;
R ² is hydroxy, (C ₁ -C ₆ )-alkoxy, (C ₂ -C ₆ )-alkenyloxy, (C ₂ -C ₆ )-alkynyloxy, (C ₁ -C ₆ )-haloalkoxy, ( C ₂ -C ₆ )-haloalkenyloxy, (C ₂ -C ₆ )-haloalkynyloxy, where the latter six groups are cyano, (C ₃ -C ₆ )-cyclo, respectively. Alkyl, (C ₃ -C ₆ )-cycloalkenyl, halo-(C ₃ -C ₆ )-cycloalkyl, halo-(C ₃ -C ₆ )-cycloalkenyl, R ⁸ (O)C, R ⁸ (R ⁸ ON=)C, R ⁸ O(O)C, R ⁹ S(O)C, (R ⁸ ) ₂ N(O)C, R ⁸ (R ⁸ O) N(O)C, (R ⁸ ) ₂ N( ^R8 )N(O)C, ^R8 (O)C( ^R8 )N(O)C, ^R9 O(O)C( ^R8 )N(O)C, ( ^R8 ) ₂ N(O)C( ^R8 )N(O)C, ^R9 (O ⁾ _2S ( ^R8 )N(O)C, R8O(O) _2S ( ^R8 )N(O)C, ( ^R8 ) _2N (O) _2S ( ^R8 )N(O)C, ^R8O , ^R8 (O)CO, R9(O) _2SO , ^R9O ( ^O )CO, (R ⁸ ) ₂ N (O) CO, (R ⁸ ) ₂ N, R ⁸ (O) C (R ⁸ ) N, R ⁹ (O) ₂ S (R ⁸ ) N, R ⁹ O (O) C (R ⁸ ) N, (R ⁸ ) ₂ N (O) C (R ⁸ ) N, R ⁸ O (O) ₂ S (R ⁸ ) N, (R ⁸ ) ₂ N (O) ₂ S (R ⁸ ) N , R ⁹ (O) _n S, R ⁸ O(O) ₂ S, (R ⁸ ) ₂ N(O) ₂ S, R ⁸ (O) C(R ⁸ ) N(O) ₂ S, R ⁹ O (O)C( ^R8 )N ⁽ O) _2S ,(R8) _2N (O)C ^{(R8)N(O)2S,R113Si,(R12O )} ₂ ⁽ _{O )} P, phenyl, heteroaryl and heterocyclyl, where the last three groups are respectively nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O substituted by m groups of the group consisting of -(C ₁ -C ₆ )-alkyl,
or
R ² represents (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-cycloalkenyloxy, phenyloxy, heteroaryloxy or heterocyclyloxy, and these five above groups each represent halogen , cyano, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C _{6 )} - )-cycloalkenyl, halo-(C ₃ -C ₆ )-cycloalkyl, halo-(C ₃ -C ₆ )-cycloalkenyl, R ⁸ (O)C, R ⁸ (R ⁸ ON=)C, R ⁸ O(O)C, R ⁹ S(O)C, (R ⁸ ) ₂ N(O)C, R ⁸ (R ⁸ O) N(O)C, (R ⁸ ) ₂ N(R ⁸ ) N( O)C, ^R8 (O)C( ^R8 ) N(O)C, ^R9 O(O)C( ^R8 ) N(O)C, ( ^R8 ) ₂ N(O)C( ^R8 )N(O)C, ^R9 (O) _2S ( ^R8 )N(O)C _, R8O(O) _2S ( ^R8 )N(O)C, ( ^R8 ) ^2N (O ⁾ ₂ S( ^R8 )N(O)C _, ^R8O , R8(O)CO, ^R9 (O)2SO, ^R9O (O)CO, ( ^R8 ) _2N (O)CO , ( ^R8 ) _2N , ^R8 (O)C( ^R8 )N, ^R9 (O) _2S (R8)N, ^R9O ( ^O )C( ^R8 )N, ( ^R8 ) ₂ N(O)C(R ⁸ )N, R ⁸ O(O) ₂ S(R ⁸ )N, (R ⁸ ) ₂ N(O) ₂ S(R ⁸ )N, R ⁹ (O) _n S , ^R8O (O) _2S , ( ^R8 )2N(O) _2S , _R8 (O)C( ^R8 )N(O) _2S , ^R9O ( ^O )C( ^R8 ) N(O ⁾ _2S , ( ^R8 ) _2N (O)C( ^R8 )N(O) _2S , _R311Si , ( ^R12O ) ₂ (O)P, phenyl, heteroaryl and heterocyclyl where the last three groups are respectively nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ to C ₆ )-alkyl, (C ₃ to C ₆ )-cycloalkyl, (C ₃ to C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ to C ₆ ) - substituted by m groups of the group consisting of alkyl, where (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, heterocyclyl, (C ₃ -C ₆ )- Cycloalkoxy, (C ₃ -C ₆ )-cycloalkenyloxy and heterocyclyloxy each independently have n oxo groups or
R ² represents R ⁸ (O) CO, R ⁹ (O) ₂ SO or R ¹⁵ R ¹⁶ C=N−O or (R ⁸ ) ₂ N−O, or
or
R ² is (R ⁸ ) ₂ N, R ⁸ (O) C (R ⁸ ) N, R ⁹ O (O) C (R ⁸ ) N, (R ⁸ ) ₂ N (O) C (R ⁸ ) N, R ⁹ (O) ₂ S (R ⁸ ) N, R ⁸ O (O) ₂ S (R ⁸ ) N, (R ⁸ ) ₂ N (O) ₂ S (R ⁸ ) N,
or
R ² represents R ⁸ (R ⁸ O)N or
R ² represents (R ¹⁷ )(R ¹⁸ )N(R ¹⁹ )N, or
or
R ² represents R ¹⁷ R ¹⁸ C=N-(R ¹⁹ )N-
R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen, nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )- Alkyl, (C ₂ -C ₆ )-alkenyl, halo-(C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, halo-(C ₃ -C ₆ )-alkynyl, (C ₃ - C ₆ )-cycloalkyl, halo-(C ₃ to C ₆ )-cycloalkyl, (C ₃ to C ₆ )-cycloalkyl-(C ₁ to C ₆ )-alkyl, halo-(C ₃ to C ₆ ) -Cycloalkyl-(C ₁ to C ₆ )-alkyl, R ⁸ (O)C, R ⁸ (R ⁸ ON=)C, R ⁸ O(O)C, (R ⁸ ) ₂ N(O)C, ^R8 ( ^R8O )N(O)C, ( ^R8 ) _2N ( ^R8 )N ^{(O)C, R8(O)C(R8 )} N(O)C, ^R9O (O )C( ^R8 )N(O)C,( ^R8 ) _2N (O)C( ^R8 )N(O)C, ^R9 (O) _2S ( ^R8 )N(O)C,R ⁸ O(O) ₂ S(R ⁸ )N(O)C, (R ⁸ ) ₂ N(O) ₂ S(R ⁸ )N(O)C, R ⁸ O, R ⁸ (O)CO, R ⁹ (O) ₂ SO, R ⁹ O (O) CO, (R ⁸ ) ₂ N (O) CO, (R ⁸ ) ₂ N, R ⁸ (O) C (R ⁸ ) N, R ⁹ (O) ₂ S(R ⁸ )N, R ⁹ O(O)C(R ⁸ )N, (R ⁸ ) ₂ N(O)C(R ⁸ )N, R ⁸ O(O) ₂ S(R ⁸ )N , (R ⁸ ) ₂ N(O) ₂ S(R ⁸ )N, R ⁹ (O) _n S, R ⁸ O(O) ₂ S, (R ⁸ ) ₂ N(O) ₂ S, R ⁸ ( O)C( ^R8 )N(O) _2S , ^R9O (O)C( ^R8 )N(O) _2S ,( ^R8 ) _2N (O)C( ^R8 )N(O) ₂ S, (R ¹² O) ₂ (O)P, R ⁸ (O)C-(C ₁ -C ₆ )-alkyl, R ⁸ O(O)C-(C ₁ -C ₆ )-alkyl, ( R ⁸ ) ₂ N(O)C-(C ₁ to C ₆ )-alkyl, (R ⁸ O)(R ⁸ )N(O)C-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(R ⁸ )N(O)C-(C ₁ to C ₆ )-alkyl, R ⁸ (O)C(R ⁸ )N(O)C-(C ₁ to C ₆ )-alkyl, R ⁹ O (O)C(R ⁸ )N(O)C-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O)C(R ⁸ )N(O)C-(C ₁ to C ₆ )-alkyl, R ⁹ (O) ₂ S(R ⁸ )N(O)C-(C ₁ ~C ₆ )-alkyl, R ⁸ O(O) ₂ S(R ⁸ )N(O)C-( C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O) ₂ S(R ⁸ )N(O)C-(C ₁ to C ₆ )-alkyl, NC-(C ₁ to C ₆ )- Alkyl, R ⁸ O-(C ₁ -C ₆ )-alkyl, R ⁸ (O)CO-(C ₁ -C ₆ )-alkyl, R ⁹ (O) ₂ SO-(C ₁ -C ₆ )-alkyl , R ⁹ O(O)CO-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O)CO-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N-(C ₁ ~C ₆ )-alkyl, R ⁸ (O)C(R ⁸ )N-(C ₁ to C ₆ )-alkyl, R ⁹ (O) ₂ S(R ⁸ )N-(C ₁ to C ₆ )- Alkyl, R ⁹ O(O)C(R ⁸ )N-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O)C(R ⁸ )N-(C ₁ to C ₆ )-alkyl , R ⁸ O(O) ₂ S(R ⁸ )N-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O) ₂ S(R ⁸ )N-(C ₁ to C ₆ )- Alkyl, R ⁹ (O) _n S-(C ₁ to C ₆ )-alkyl, R ⁸ O(O) ₂ S-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O) ₂ S -(C ₁ to C ₆ )-alkyl, R ⁸ (O)C(R ⁸ )N(O) ₂ S-(C ₁ to C ₆ )-alkyl, R ⁹ O(O)C(R ⁸ )N (O) ₂ S-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O)C(R ⁸ )N(O) ₂ S-(C ₁ to C ₆ )-alkyl, (R ¹² O) ₂ (O)P-(C ₁ -C ₆ )-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl or represents heterocyclyl-(C ₁ -C ₆ )-alkyl, where these latter six groups are respectively nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ ～C ₆ )-Alkyl, (C ₃ ～C ₆ )-Cycloalkyl, R ⁸ O(O)C, (R ⁸ ) ₂ N(O)C, R ⁸ O, (R ⁸ ) ₂ N, R ⁹ Substituted by m groups of the group consisting of (O) _n S, R ⁸ O(O) ₂ S, (R ⁸ ) ₂ N(O) ₂ S and R ⁸ O-(C ₁ -C ₆ )-alkyl , where cycloalkyl and heterocyclyl each independently have n oxo groups,
R ⁸ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkenyl-(C ₁ -C ₆ )-alkyl, (C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, (C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkenyl- (C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl or (C ₁ -C ₆ )-alkylthio-(C ₁ -C ₆ )-alkyl; The 12 groups have s halogen atoms, or
or
R ⁸ is phenyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl- O-(C ₁ -C ₆ )-alkyl, heteroaryl-O-(C ₁ -C ₆ )-alkyl, heterocyclyl-O-(C ₁ -C ₆ )-alkyl, phenyl-N(R ¹⁰ )-( _C1 - _C6 )-alkyl, heteroaryl-N( ^R10 )-(C1 _{- C6} )-alkyl, heterocyclyl-N( ^R10 )-( _C1 - _C6 )-alkyl, phenyl-S( O) _n -(C ₁ -C ₆ )-alkyl, heteroaryl-S(O) _n -(C ₁ -C ₆ )-alkyl or heterocyclyl-S(O) _n -(C ₁ -C ₆ )-alkyl , where the groups are nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cyclo, respectively. Alkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S , R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl,
and (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl and heterocyclyl each independently have n oxo groups,
or
The ^R8 group represents one or more heteroatoms and rings to which they are attached, in particular heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, form heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn represents nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C 6 )-alkyl, or heterocyclenylheteroaryl. ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl and substituted by m groups of the group consisting of oxo,
R ⁹ is (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-Cycloalkenyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkenyl-(C ₁ -C ₆ )-alkyl, (C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, (C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkenyl-(C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl or (C ₁ to C ₆ )-alkylthio-(C ₁ to C ₆ )-alkyl, where the group is s has a halogen atom, or
or
R ⁹ is phenyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl- O-(C ₁ -C ₆ )-alkyl, heteroaryl-O-(C ₁ -C ₆ )-alkyl, heterocyclyl-O-(C ₁ -C ₆ )-alkyl, phenyl-N(R ¹⁰ )-( _C1 - _C6 )-alkyl, heteroaryl-N( ^R10 )-(C1 _{- C6} )-alkyl, heterocyclyl-N( ^R10 )-( _C1 - _C6 )-alkyl, phenyl-S( O) _n -(C ₁ -C ₆ )-alkyl, heteroaryl-S(O) _n -(C ₁ -C ₆ )-alkyl or heterocyclyl-S(O) _n -(C ₁ -C ₆ )-alkyl , where the groups are nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cyclo, respectively. Alkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S , R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl,
and (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl and heterocyclyl each independently have n oxo groups,
R ¹⁰ is hydrogen, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ - _C6 )-cycloalkyl, ( _C3 - _C6 )-cycloalkyl-( _C1 - _C6 )-alkyl or phenyl;
R ¹¹ is (C ₁ to C ₆ )-alkyl, halo-(C ₁ to C ₆ )-alkyl, (C ₂ to C ₆ )-alkenyl, (C ₂ to C ₆ )-alkynyl, (C ₃ to C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl or phenyl,
R ¹² represents hydrogen or (C ₁ -C ₄ )-alkyl;
R ¹³ and R ¹⁴ are each independently hydrogen, (C ₁ -C ₆ )-alkyl, hydroxy, (C ₁ -C ₆ )-alkoxy, (R ⁸ ) ₂ N, halo-(C ₁ -C ₆ )-alkoxy, halogen, halo-(C ₁ -C ₆ )-alkyl, cyano, R ⁸ O(O)C or (R ⁸ ) ₂ N(O)C,
or
R ¹³ and R ¹⁴ together with the carbon atom to which they are attached form a (C ₃ -C ₈ )-cycloalkyl group;
R ¹⁵ and R ¹⁶ each independently represent (C ₁ -C ₆ )-alkyl, phenyl, (C ₃ -C ₆ )-cycloalkyl, heteroaryl or heterocyclyl;
R ¹⁷ and R ¹⁸ and R ¹⁹ are independently R ⁸ or R ⁹ S(O) ₂ , (R ⁸ ) ₂ NS(O) ₂ , R ⁸ OS(O) ₂ , R ⁹ C(O), (R ⁸ ) ₂ NC(O), (R ⁸ ) ₂ NC(S), R ⁸ OC(O), R ⁸ OC(O) C(O), (R ⁸ ) ₂ NC(O) C(O ) or
or (R ¹⁷ and R ¹⁸ ) or (R ¹⁷ and R ¹⁹ ) groups include one or more heteroatoms and rings to which they are attached, specifically heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, aryl forming heterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn represents nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, ( R ¹⁰ ) ₂ N(O) C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and substituted by m groups of the group consisting of R ¹⁰ O-(C ₁ -C ₆ )-alkyl and oxo;
m represents 0, 1, 2, 3, 4 or 5;
n represents 0, 1 or 2;
s represents 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11)
and a pesticide-acceptable salt thereof.

Compounds of formula (I) can form salts. Salts may be formed by the action of bases on compounds of formula (I) having acidic hydrogen atoms. Suitable bases are, for example, organic amines (such as trialkylamines, morpholines, piperidine or pyridine), and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, especially sodium hydroxide, water Potassium oxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate. These salts contain acidic hydrogen with agriculturally suitable cations, such as metal salts, especially alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts. salts, for example by cations of the formula [NRR'R''R''' ^] It is a replaced compound. Alkylsulfonium and alkylsulfoxonium salts such as (C _{1 -C 4} )-trialkylsulfonium and (C 1 -C ₄ )-trialkylsulfoxonium salts are also suitable.

Compounds of formula (I) may be added to suitable inorganic or organic acids, such as mineral acids, such as HCl, HBr, _H2SO4 , _{H3PO4 or HNO3} , or organic acids, such as carboxylic acids, such as formic acid, acetic acid, _etc. , propionic acid, oxalic acid, lactic acid or salicylic acid, or a sulfonic acid such as p-toluenesulfonic acid to a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. I can do it. In such cases, these salts contain the conjugate base of the acid as the anion.

Suitable substituents that are present in deprotonated form, such as sulfonic or carboxylic acids, may form internal salts with groups whose moieties can be protonated, such as amino groups.

Alkyl is a saturated straight-chain or branched hydrocarbyl radical with the number of carbon atoms specified in each case, for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1- Dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl means C ₁ -C ₆ -alkyl such as.

Halogen-substituted alkyl refers to straight-chain or branched alkyl groups in which some or all of the hydrogen atoms of these groups may be replaced by halogen atoms, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, Difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- Trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1, means C ₁ -C ₂ -haloalkyl such as 1-trifluoroprop-2-yl.

Alkenyl is in each case an unsaturated straight-chain or branched hydrocarbyl group with the stated number of carbon atoms and one double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl, 1- Methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2- Butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl- 1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-Methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3- Methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl- 4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3, 3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1- Represents C ₂ -C ₆ -alkenyl such as propenyl and 1-ethyl-2-methyl-2-propenyl.

Alkynyl is a straight-chain or branched hydrocarbyl group in each case with the specified number of carbon atoms and one triple bond in any position, for example ethynyl, 1-propynyl, 2-propynyl (or propargyl), 1- Butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl-1-butynyl, 1-methyl-2-butynyl, 1-Methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 3-methyl-1-pentynyl, 4-methyl-1-pentynyl, 1-methyl-2-pentynyl, 4-methyl-2-pentynyl, 1-methyl-3-pentynyl, 2-methyl-3- Pentynyl, 1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2- Dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and It means C ₂ -C ₆ -alkynyl such as 1-ethyl-1-methyl-2-propynyl.

Cycloalkyl means a carbocyclic saturated ring system having preferably 3 to 8 ring carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. In the case of optionally substituted cycloalkyl, ring systems with substituents are included, and also substituents with double bonds on the cycloalkyl group, for example alkylidene groups such as methylidene.

In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems such as bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2. 1.0] Pentan-1-yl, Bicyclo[2.1.0] Pentan-2-yl, Bicyclo[2.1.0] Pentan-5-yl, Bicyclo[2.2.1] Heptan-2-yl. Also included are yl (norbornyl), adamantan-1-yl and adamantan-2-yl.

In the case of substituted cycloalkyl, spirocycloaliphatic systems such as spiro[2.2]pent-1-yl, spiro[2.3]hex-1-yl and spiro[2.3]hex-4-yl, Also included is 3-spiro[2.3]hex-5-yl.

Cycloalkenyl preferably refers to carbocyclic, non-aromatic, partially unsaturated ring systems having 4-8 carbon atoms, such as 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3 - means cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl, and a substituent containing a double bond in the cycloalkenyl group , also includes alkylidene groups such as, for example, methylidene. In the case of optionally substituted cycloalkenyl, the elucidation for substituted cycloalkyl applies mutatis mutandis.

Alkoxy is a saturated straight-chain or branched alkoxy group with the number of carbon atoms specified in each case, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1- Dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1- Methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and C ₁ -C ₆ -alkoxy such as 1-ethyl-2-methylpropoxy. Halogen-substituted alkoxy refers to straight-chain or branched alkoxy groups with the number of carbon atoms specified in each case, in which some or all of the hydrogen atoms of these groups may be replaced by the halogen atoms specified above; For example, chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-1,2-difluoroethoxy, 2,2-dichloro-2- It means C ₁ -C 2 -haloalkoxy such as fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop- ₂ -oxy.

Aryl is fluorine, chlorine, bromine, iodine, cyano, hydroxy, (C ₁ -C ₃ )-alkyl, (C ₁ -C ₃ )-alkoxy, (C ₃ -C ₄ )-cycloalkyl, (C ₂ - It means phenyl optionally substituted by 0 to 5 groups of the group consisting of C 3 )-alkenyl or (C _{2 -C 3} )-alkynyl.

A heterocyclic group (heterocyclyl) is saturated, unsaturated, partially saturated, or heteroaromatic and may be unsubstituted or substituted, and if substituted, the point of attachment is located on a ring atom. at least one heterocycle (=carbocycle in which at least one carbon atom is replaced by a heteroatom, preferably of the group N, O, S, P). When a heterocyclyl group or heterocycle is optionally substituted, it may be fused to another carbocycle or heterocycle. In the case of optionally substituted heterocyclyl, polycyclic systems such as 8-azabicyclo[3.2.1]octanyl, 8-azabicyclo[2.2.2]octanyl or 1-azabicyclo[2.2.1 ] Also includes heptyl. Optionally substituted heterocyclyl also includes spiro ring systems, such as 1-oxa-5-azaspiro[2.3]hexyl. Unless otherwise defined, heterocycle preferably has 3 to 9 ring atoms, especially 3 to 6 ring atoms and 1 or more, preferably 1 to 4, especially 1, 2 or 3 heterocycles. Atoms, preferably heteroatoms of the group N, O and S are included within the heterocycle, but the two oxygen atoms are not directly adjacent. Examples for one heteroatom of the group N, O and S: 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or -3-yl, 2, 3-dihydro-1H-pyrrole-1- or -2- or -3- or -4- or -5-yl; 2,5-dihydro-1H-pyrrole-1- or -2- or -3-yl; 1- or 2- or 3- or 4-piperidinyl; 2, 3, 4, 5-tetrahydropyridine-2- or -3- or -4- or -5-yl or -6-yl; 1,2,3 , 6-tetrahydropyridine-1- or -2- or -3- or -4- or -5- or -6-yl; 1,2,3,4-tetrahydropyridine-1- or -2- or -3 - or -4- or -5- or -6-yl; 1,4-dihydropyridine-1- or -2- or -3- or -4-yl; 2,3-dihydropyridine-2- or -3- or -4- or -5- or -6-yl; 2,5-dihydropyridine-2- or -3- or -4- or -5- or -6-yl, 1- or 2- or 3- or 4- Azepanil; 2,3,4,5-tetrahydro-1H-azepin-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4, 7-tetrahydro-1H-azepine-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,6,7-tetrahydro-1H-azepine- 1- or -2- or -3- or -4-yl; 3,4,5,6-tetrahydro-2H-azepine-2- or -3- or -4- or -5- or -6- or - 7-yl; 4,5-dihydro-1H-azepine-1- or -2- or -3- or -4-yl; 2,5-dihydro-1H-azepine-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2,7-dihydro-1H-azepine-1- or -2- or -3- or -4-yl; 2,3-dihydro- 1H-azepine-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 3,4-dihydro-2H-azepine-2- or -3- or - 4- or -5- or -6- or -7-yl; 3,6-dihydro-2H-azepin-2- or -3- or -4- or -5- or -6- or -7-yl; 5,6-dihydro-2H-azepine-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydro-3H-azepine-2- or -3- or -4- or -5- or -6- or -7-yl; 1H-azepine-1- or -2- or -3- or -4- or -5- or -6- or -7-yl; 2H-azepine-2- or -3- or -4- or -5- or -6- or -7-yl; 3H-azepine-2- or -3- or -4- or -5- or -6- or -7-yl; 4H-azepine-2- or -3- or -4- or -5- or -6- or -7-yl, 2- or 3-oxolanyl (=2- or 3-tetrahydrofuranyl) ; 2,3-dihydrofuran-2- or -3- or -4- or -5-yl; 2,5-dihydrofuran-2- or -3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H -pyran-2- or -3- or -4- or -5- or -6-yl; 2H-pyran-2- or -3- or -4- or -5- or -6-yl; 4H-pyran -2- or -3- or -4-yl, 2- or 3- or 4-oxepanyl; 2,3,4,5-tetrahydroxepin -2- or -3- or -4- or -5- or -6- or -7-yl; 2,3,4,7-tetrahydroxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2,3 , 6,7-tetrahydroxepin-2- or -3- or -4-yl; 2,3-dihydroxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 4,5-dihydroxepin-2- or -3- or -4-yl; 2,5-dihydroxepin-2- or -3- or -4- or -5- or -6- or -7-yl; oxepin-2- or -3- or -4- or -5- or -6- or -7-yl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophene -2- or -3- or -4- or -5-yl; 2,5-dihydrothiophen-2- or -3-yl; tetrahydro-2H-thiopyran-2- or -3- or -4-yl; 3,4-dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 3,6-dihydro-2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 2H-thiopyran-2- or -3- or -4- or -5- or -6-yl; 4H-thiopyran-2- or -3- or -4-yl; be. Preferred 3- and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1, It is 3-dioxetan-2-yl. Further examples of "heterocyclyl" include partially hydrogenated or fully hydrogenated heterocyclic groups having two heteroatoms of the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl. ; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazole-1- or 3- or 4- or 5-yl; 2,3-dihydro- 1H-pyrazole-1- or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4- imidazolidinyl; 2,3-dihydro-1H-imidazole-1- or 2- or 3 - or 4-yl; 2,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1- or 2- or 4- or 5- yl; hexahydropyridazin-1- or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazin-1- or 2- or 3- or 4- or 5- or 6-yl; 1 , 2,3,6-tetrahydropyridazine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4,5,6-tetrahydropyridazine-1- or 3- or 4- or 5 - or 6-yl; 3,4,5,6-tetrahydropyridazin-3- or 4- or 5-yl; 4,5-dihydropyridazin-3- or 4-yl; 3,4-dihydropyridazin-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazin-3- or 4-yl; 1,6-dihydropyridazin-1- or 3- or 4- or 5- or 6-yl; hexahydro Pyrimidine-1- or 2- or 3- or 4-yl; 1,4,5,6-tetrahydropyrimidine-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6- Tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,3,4-tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl; 1 , 6-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2-dihydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 2,5-dihydro Pyrimidin-2- or 4- or 5-yl; 4,5-dihydropyrimidin- 4- or 5- or 6-yl; 1,4-dihydropyrimidin-1- or 2- or 4- or 5- or 6- 1- or 2- or 3-piperazinyl; 1- or 2- or 3- or 5- or 6-yl; 1, 2, 3, 4-tetrahydropyrazine- 1- or 2- or 3- or 4- or 5- or 6-yl; 1,2-dihydropyrazine-1- or 2- or 3- or 5- or 6-yl; 1,4-dihydropyrazine-1 - or 2- or 3-yl; 2,3-dihydropyrazin-2- or 3- or 5- or 6-yl; 2,5-dihydropyrazin-2- or 3-yl; 1,3-dioxolane-2 - or 4- or 5-yl; 1,3-dioxol-2- or 4-yl; 1,3-dioxane-2- or 4- or 5-yl; 4H-1,3-dioxin-2- or 4 - or 5- or 6-yl; 1,4-dioxane-2- or 3- or 5- or 6-yl; 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6 -yl; 1,4-dioxin-2- or 3-yl; 1,2-dithiolan-3- or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl; 1,3 -dithioran-2- or 4-yl; 1,3-dithiol-2- or 4-yl; 1,2-dithian-3- or 4-yl; 3,4-dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro-1,2-dithiin-3- or 4-yl; 1,2-dithiin-3- or 4-yl; 1,3-dithian-2 - or 4- or 5-yl; 4H-1,3-dithiin-2- or 4- or 5- or 6-yl; isoxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro Isoxazole-2- or 3- or 4- or 5-yl; 2,5-dihydroisoxazole-2- or 3- or 4- or 5-yl; 4,5-dihydroisoxazole-3- or 4- or 5-yl; 1,3-oxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-oxazole-2- or 3- or 4- or 5- yl; 2,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-oxazol-2- or 4- or 5-yl; 1,2- Oxazinane-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 3, 6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,2-oxazine-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 2H-1,2-oxazine-2- or 3- or 4 - or 5- or 6-yl; 6H-1,2-oxazin-3- or 4- or 5- or 6-yl; 4H-1,2-oxazin-3- or 4- or 5- or 6-yl ; 1,3-oxazinane-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6 -yl; 3,6-dihydro-2H-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,3-oxazine-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-oxazine-2- or 4- or 5- or 6-yl; 2H-1,3-oxazine-2- or 4- or 5- or 6-yl; 6H-1,3-oxazin-2- or 4- or 5- or 6-yl; 4H-1,3-oxazin-2- or 4- or 5- or 6-yl; Morpholine-2- or 3- or 4-yl; 3,4-dihydro-2H-1,4-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H- 1,4-oxazin-2- or 3- or 5- or 6-yl; 2H-1,4-oxazin-2- or 3- or 5- or 6-yl; 4H-1,4-oxazin-2- or 3-yl; 1,2-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetra

Hydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,2-oxazepine-2- or 3- or 4 - or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5 , 6,7-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro -1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 1,3-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1, 3-Oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7 -tetrahydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-1,3-oxazepine- 2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro- 1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7- Tetrahydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,4-oxazepine-2- or 3- or 5- or 6 - or 7-yl; 4,5,6,7-tetrahydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,4 -Oxazepine-2- or 3- or 5- or 6- or 7-yl; 2,5-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; -dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 4,5-dihydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6 - or 7-yl; 4,7-dihydro-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,4-oxazepine-2 - or 3- or 5- or 6- or 7-yl; 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; isothiazolidine-2- or 3- or 4- or 5 -yl; 2,3-dihydroisothiazol-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazol-2- or 3- or 4- or 5-yl; 4,5-dihydro Isothiazol-3- or 4- or 5-yl; 1,3-thiazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-thiazole-2- or 3- or 4- or 5-yl; 2,5-dihydro-1,3-thiazol-2- or 4- or 5-yl; 4,5-dihydro-1,3-thiazol-2- or 4- or 5-yl ; 1,3-thiazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-1,3-thiazine-2- or 3- or 4- or 5- or 6 -yl; 3,6-dihydro-2H-1,3-thiazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-1,3-thiazin-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-thiazin-2- or 4- or 5- or 6-yl; 2H-1,3-thiazin-2- or 4- or 5- or 6-yl; 6H-1,3-thiazin-2- or 4- or 5- or 6-yl; 4H-1,3-thiazin-2- or 4- or 5- or 6-yl; be. Further examples of "heterocyclyl" are partially hydrogenated or fully hydrogenated heterocyclic groups having three heteroatoms of the group N, O and S, such as 1,4,2-dioxazolidine-2- or -3- or -5-yl; 1,4,2-dioxazol-3- or -5-yl; 1,4,2-dioxazinan-2- or -3- or -5- or -6-yl; 5,6-dihydro-1,4,2-dioxazin-3- or -5- or -6-yl; 1,4,2-dioxazin-3- or -5- or -6-yl; 1,4, 2-dioxazepine-2- or -3- or -5- or -6- or -7-yl; 6,7-dihydro-5H-1,4,2-dioxazepine-3- or -5- or -6- or -7-yl; 2,3-dihydro-7H-1,4,2-dioxazepine-2- or -3- or -5- or -6- or -7-yl; 2,3-dihydro-5H- 1,4,2-dioxazepine-2- or -3- or -5- or -6- or -7-yl; 5H-1,4,2-dioxazepine-3- or -5- or -6- or - 7-yl; 7H-1,4,2-dioxazepin-3- or -5- or -6- or -7-yl. Examples of optionally further substituted heterocycle structures are also listed below:

The heterocycles listed above are, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, Heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl , alkylalkynyl, trisalkylsilylalkynyl, nitro, amino, cyano, haloalkoxy, haloalkylthio, alkylthio, hydrothio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy, heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio, hetero Aryloxy, bisalkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl(alkyl)amino, aminocarbonyl, alkylaminocarbonyl, bisalkylaminocarbonyl, Preferably, it is substituted by cycloalkylaminocarbonyl, hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl, arylalkoxycarbonylalkylaminocarbonyl.

"Arylheterocyclenyl" refers to an aryl attached to a heterocyclenyl, where the point of attachment is located on a ring atom. Particular preference is given to when aryl represents phenyl and the heterocyclenyl ring consists of 5 to 6 ring atoms. The arylheterocyclenyl is attached through any available atom of the heterocyclenyl. The prefix aza, oxa or thio before the heterocyclenyl unit of arylheterocyclenyl defines a nitrogen, oxygen or sulfur atom present as at least one ring atom. The nitrogen of the arylheterocyclenyl can be a basic nitrogen atom. The nitrogen or sulfur ring atom of the arylheterocyclenyl may be optionally oxidized to the corresponding N-oxide, S-oxide or S,S-dioxide. Examples of arylheterocyclenyl include 3H-indolinyl, 1H-2-oxoquinolyl, 2H-1-oxoisoquinolyl or 1,2-dihydroisoquinolyl.

"Arylheterocyclyl" refers to an aryl attached to a heterocyclyl, where the point of attachment is located on a ring atom. Particular preference is given to when aryl represents phenyl and the heterocyclyl ring consists of 5 to 6 ring atoms. An arylheterocyclyl is attached through any available atom of the heterocyclyl. The prefix aza, oxa or thio before the heterocyclyl unit of arylheterocyclyl defines a nitrogen, oxygen or sulfur atom present as at least one ring atom. The arylheterocyclyl nitrogen can be a basic nitrogen atom. The nitrogen or sulfur ring atom of the arylheterocyclyl may be optionally oxidized to the corresponding N-oxide, S-oxide or S,S-dioxide. Examples of arylheterocyclyl include indolinyl, 1,2,3,4-tetrahydroquinolinyl or 1,2,3,4-tetrahydroisoquinolinyl.

Cyclenyl includes, for example, a non-aromatic monocyclic or polycyclic ring system of 3 to 10 carbon atoms, preferably 5 to 10 carbon atoms and containing at least one carbon-carbon double bond. represent. Among ring systems, 5- and 6-membered rings are preferred. Examples of monocyclic cycloalkenyl include cyclopentenyl, cyclohexenyl and cycloheptenyl.

"Cycloalkenylaryl" refers to an aryl attached to a cycloalkenyl, where the point of attachment is located on a ring atom. Particular preference is given to when aryl represents phenyl and cycloalkenyl consists of 5 to 6 ring atoms. Cycloalkenyl aryl is bonded via any bondable atom of cycloalkenyl.

"Cycloalkenylheteroaryl" refers to a heteroaryl attached to a cycloalkenyl, where the point of attachment is located on a ring atom. Particular preference is given to when heteroaryl consists of 5 to 6 ring atoms and cycloalkenyl consists of 5 to 6 ring atoms. Cycloalkenyl aryl is bonded via any bondable atom of cycloalkenyl. The nitrogen of a heteroaryl can be a basic nitrogen atom.

The prefix aza, oxa or thio before the heteroaryl unit of cycloalkenylheteroaryl defines a nitrogen, oxygen or sulfur atom present as at least one ring atom. A nitrogen ring atom of a heteroaryl can be optionally oxidized to the corresponding N-oxide.

If the underlying structure is substituted by "one or more radicals" from a list of radicals (= group) or a group of commonly defined radicals, this in each case also includes simultaneous substitution with multiple identical and/or structurally different groups.

In the case of a partially or fully saturated nitrogen heterocycle, it may be linked to the rest of the molecule via either carbon or nitrogen.

Suitable substituents for substituted heterocyclic groups are the substituents specified further below, and also oxo and thioxo. In that case, the oxo group as a substituent on a ring carbon atom is, for example, a heterocyclic carbonyl group. As a result, lactones and lactams are also preferably included. Oxo groups may also be present on ring heteroatoms, which may be present in different oxidation states, for example in the case of N and S, in which case, for example, the divalent -N(O )-, -S(O)- (abbreviated SO) and -S(O) ₂ - (abbreviated SO ₂ ) groups are formed. In the case of N(O) and S(O) groups, both enantiomers are included in each case.

According to the invention, the expression "heteroaryl" refers to heteroaromatic compounds, i.e. fully unsaturated aromatic heterocyclic compounds, preferably containing 1 to 4, preferably 1 or 2, identical or different heteroatoms. , preferably refers to a 5- to 7-membered ring having O, S or N. Heteroaryls of the invention include, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl. ;thien-3-yl, 1H-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl; 1H-pyrazol-1-yl; 1H-pyrazole -3-yl; 1H-pyrazol-4-yl; 1H-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H -1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazole -1-yl, 1H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl, 1,2,4-oxadiazol-3-yl, 1,2 , 4-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5 -yl, 1,2,5-oxadiazol-3-yl, azepinyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidine -2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3 -yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl , 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1, 3-oxazol-2-yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 , 3-thiazol-2-yl, 1,3-thiazol-4-yl, 1,3-thiazol-5-yl, oxepinyl, thiepinyl, 1,2,4-triazolonyl and 1,2,4-diazepinyl, 2H -1,2,3,4-tetrazol-5-yl, 1H-1,2,3,4-tetrazol-5-yl, 1,2,3,4-oxatriazol-5-yl, 1,2, 3,4-thiatriazol-5-yl, 1,2,3,5-oxatriazol-4-yl, and 1,2,3,5-thiatriazol-4-yl. The heteroaryl groups of the invention may also be substituted by one or more of the same or different groups. If two adjacent carbon atoms are part of a further aromatic ring, the system is a fused heteroaromatic system, for example a benzofused or polyannealed heteroaromatic. Preferred examples are quinolines (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl) ; isoquinoline (e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; Quinazoline; Cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; Phthalazine; Pyridopyrazine; Pyridopyrimidine; Pyrido Pyridazine; pteridine; pyrimidopyrimidine. Examples of heteroaryl are also 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H-indol-5-yl, 1H-indole -6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6 -yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzo Thiophen-6-yl, 1-benzothiophen-7-yl, 1H-indazol-1-yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazole -6-yl, 1H-indazol-7-yl, 2H-indazol-2-yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-indazol-6 -yl, 2H-indazol-7-yl, 2H-isoindol-2-yl, 2H-isoindol-1-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H-iso Indol-5-yl, 2H-isoindol-6-yl; 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl , 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H-benzimidazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, 1,3-benzoxazol-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazole -4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,2-benzoisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,2-benzisoxazol-6-yl, 1,2-benzisoxazol-7-yl, 1, 2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1,2- It is a 5- or 6-membered benzo-fused ring of the group benzisothiazol-7-yl.

The term "halogen" means fluorine, chlorine, bromine or iodine. When the term is used radically, "halogen" means a fluorine, chlorine, bromine or iodine atom.

Depending on the nature of the substituents and the way they are attached, compounds of formula (I) may exist as stereoisomers. For example, if one or more asymmetrically substituted carbon atoms and/or sulfoxides are present, enantiomers and diastereomers may occur. The stereoisomers can be obtained from the mixture obtained in the preparation by conventional separation methods, such as chromatographic separation methods. Similarly, it is also possible to selectively prepare stereoisomers by using stereoselective reactions with optically active starting materials and/or auxiliaries.

The invention also relates to all stereoisomers encompassed by formula (I) but not specifically defined and mixtures thereof. However, in the following text, for the sake of simplicity, we will always refer to compounds of formula (I), which means not only the pure compounds, but also, where appropriate, mixtures with various amounts of isomeric compounds. be understood.

This also refers to the tautomeric structure of compound (I) due to the fact that at least one R ¹³ or R ¹⁴ group is hydrogen.

In all formulas specified below, the substituents and symbols have the same meaning as given in formula (I), unless defined differently. The arrow in a chemical formula indicates the point at which it attaches to the rest of the molecule.

（式中、
Xは、C（R¹³）（R¹⁴）を表し、
R¹は、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニルまたはヘテロシクリルを表し、ここで、これらの3つの基は、各々、ハロゲン、（C₁～C₆）－アルキルおよびハロ－（C₁～C₆）－アルキルからなる群のs個の基により置換され、ここでシクロアルキル、シクロアルケニルおよびヘテロシクリルは、各々独立に、n個のオキソ基を有し、
R²は、ヒドロキシ、（C₁～C₆）－アルコキシ、（C₂～C₆）－アルケニルオキシ、（C₂～C₆）－アルキニルオキシ、（C₁～C₆）－ハロアルコキシ、（C₂～C₆）－ハロアルケニルオキシ、（C₂～C₆）－ハロアルキニルオキシを表し、ここで、これらの後の6つの基は、シアノ、R⁸（O）C、R⁸O（O）C、（R⁸）₂N（O）C、R⁸（R⁸O）N（O）C、（R⁸）₂N（R⁸）N（O）C、R⁸O、R⁸（O）CO、R⁹（O）₂SO、（R⁸）₂N、R⁹（O）_nS、フェニル、ヘテロアリールおよびヘテロシクリルからなる群の基により置換されており、ここで、これらの後の3つの基は、各々、ニトロ、ハロゲン、シアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルからなる群のm個の基により置換されており、ここで（C₃～C₆）－シクロアルキルおよびヘテロシクリルは、各々独立にn個のオキソ基を有するか、
または
R²は、（C₃～C₆）－シクロアルコキシ、（C₃～C₆）－シクロアルケニルオキシ、フェニルオキシ、ヘテロアリールオキシまたはヘテロシクリルオキシを表し、ここでこれらの5つの上記基は、各々、ハロゲン、シアノ、（C₁～C₆）－アルキル、（C₂～C₆）－アルケニル、（C₂～C₆）－アルキニル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、ハロ－（C₃～C₆）－シクロアルキル、ハロ－（C₃～C₆）－シクロアルケニル、R⁸（O）C、R⁸O（O）C、（R⁸）₂N（O）C、R⁸（R⁸O）N（O）C、（R⁸）₂N（R⁸）N（O）C、R⁸O、R⁸（O）CO、R⁹（O）₂SO、（R⁸）₂N、R⁹（O）_nS、フェニル、ヘテロアリールおよびヘテロシクリルからなる群のs個の基により置換され、
ここで、これらの後の3つの基は、各々、ニトロ、ハロゲン、シアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルからなる群のm個の基により置換されており、ここで（C₃～C₆）－シクロアルコキシ、（C₃～C₆）－シクロアルキルおよびヘテロシクリルは、各々独立にn個のオキソ基を有するか、
または
R²は、（R⁸）₂N、R⁸（O）C（R⁸）N、R⁹O（O）C（R⁸）N、（R⁸）₂N（O）C（R⁸）N、R⁹（O）₂S（R⁸）N、R⁸O（O）₂S（R⁸）N、（R⁸）₂N（O）₂S（R⁸）Nを表すか、
または
R²は、R⁸（R⁸O）Nを表すか
または
R²は、（R¹⁷）（R¹⁸）N（R¹⁹）Nを表すか、
または
R²は、R¹⁷R¹⁸C＝N－（R¹⁹）N－を表し、
R³、R⁴、R⁵、R⁶およびR⁷は、各々独立に、水素、ニトロ、ハロゲン、シアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₂～C₆）－アルケニル、（C₂～C₆）－アルキニル、（C₃～C₆）－シクロアルキル、ハロ－（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、ハロ－（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、R⁸（O）C、R⁸（R⁸ON＝）C、R⁸O（O）C、（R⁸）₂N（O）C、R⁸O、（R⁸）₂N、R⁸（O）C（R⁸）N、R⁹（O）₂S（R⁸）N、R⁹O（O）C（R⁸）N、（R⁸）₂N（O）C（R⁸）N、R⁹（O）_nS、R⁸O（O）₂S、（R⁸）₂N（O）₂S、（R¹²O）₂（O）P、R⁸（O）C－（C₁～C₆）－アルキル、R⁸O（O）C－（C₁～C₆）－アルキル、（R⁸）₂N（O）C－（C₁～C₆）－アルキル、NC－（C₁～C₆）－アルキル、R⁸O－（C₁～C₆）－アルキル、（R⁸）₂N－（C₁～C₆）－アルキル、R⁸（O）C（R⁸）N－（C₁～C₆）－アルキル、R⁹（O）₂S（R⁸）N－（C₁～C₆）－アルキル、R⁹O（O）C（R⁸）N－（C₁～C₆）－アルキル、（R⁸）₂N（O）C（R⁸）N－（C₁～C₆）－アルキル、R⁹（O）_nS－（C₁～C₆）－アルキル、R⁸O（O）₂S－（C₁～C₆）－アルキル、（R⁸）₂N（O）₂S－（C₁～C₆）－アルキル、（R¹²O）₂（O）P－（C₁～C₆）－アルキル、フェニル、ヘテロアリール、ヘテロシクリル、フェニル－（C₁～C₆）－アルキル、ヘテロアリール－（C₁～C₆）－アルキル、ヘテロシクリル－（C₁～C₆）－アルキルを表し、ここで、これらの後の6つの基は、各々、ニトロ、ハロゲン、シアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、R⁸O、（R⁸）₂N、R⁹（O）_nS、R⁸O（O）₂S、（R⁸）₂N（O）₂SおよびR⁸O－（C₁～C₆）－アルキルからなる群のm個の基によって置換されており、ここでヘテロシクリルはn個のオキソ基を有し、
R⁸は、水素、（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、フェニル、フェニル－（C₁～C₆）－アルキル、ヘテロアリール、ヘテロアリール－（C₁～C₆）－アルキル、ヘテロシクリル、ヘテロシクリル－（C₁～C₆）－アルキル、フェニル－O－（C₁～C₆）－アルキル、ヘテロアリール－O－（C₁～C₆）－アルキルまたはヘテロシクリル－O－（C₁～C₆）－アルキルであり、ここで、これらの後の9つの基は、各々、ニトロ、ハロゲン、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nSおよびR¹⁰O－（C₁～C₆）－アルキルからなる群のm個の基により置換されており、ここでヘテロシクリルはn個のオキソ基を有するか、
または
2つのR⁸基は、それらが結合している1個または複数のヘテロ原子と環、具体的には、ヘテロシクリル、ヘテロシクレニル、ヘテロアリール、アリールヘテロシクリル、アリールヘテロシクレニル、ヘテロアリールヘテロシクリル、ヘテロアリールヘテロシクレニル、ヘテロシクリルヘテロアリールまたはヘテロシクレニルヘテロアリールを形成し、ここで、これらの環の各々は、今度はハロゲン、シアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルおよびオキソからなる群のm個の基によって置換されており、
R⁹は、（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、フェニル、フェニル－（C₁～C₆）－アルキル、ヘテロアリール、ヘテロアリール－（C₁～C₆）－アルキル、ヘテロシクリル、ヘテロシクリル－（C₁～C₆）－アルキル、フェニル－O－（C₁～C₆）－アルキル、ヘテロアリール－O－（C₁～C₆）－アルキルまたはヘテロシクリル－O－（C₁～C₆）－アルキルを表し、ここで、これらの後の9つの基は各々、ニトロ、ハロゲン、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nSおよびR¹⁰O－（C₁～C₆）－アルキルからなる群のm個の基により置換されており、ここでヘテロシクリルはn個のオキソ基を有し、
R¹⁰は、水素または（C₁～C₆）－アルキルを表し、
R¹¹は、（C₁～C₆）－アルキルを表し、
R¹²は、（C1～C4）－アルキルを表し、
R¹³およびR¹⁴は、各々独立に、水素、（C₁～C₆）－アルキル、ヒドロキシ、（C₁～C₆）－アルコキシ、（R⁸）₂N、ハロ－（C₁～C₆）－アルコキシ、ハロゲン、ハロ－（C₁～C₆）－アルキル、シアノ、R⁸O（O）Cまたは（R⁸）₂N（O）Cを表すか、
または
R¹³およびR¹⁴は、それらが結合している炭素原子とともに（C₃～C₈）－シクロアルキル基を形成し、
R¹⁵およびR¹⁶は、各々独立に、（C₁～C₆）－アルキル、フェニル、（C₃～C₆）－シクロアルキル、ヘテロアリールまたはヘテロシクリルを表し、
R¹⁷、R¹⁸およびR¹⁹は、独立に、R⁸またはR⁹S（O）₂、（R⁸）₂NS（O）₂、R⁸OS（O）₂、R⁹C（O）、（R⁸）₂NC（O）、（R⁸）₂NC（S）、R⁸OC（O）、R⁸OC（O）C（O）、（R⁸）₂NC（O）C（O）を表すか、または
（R¹⁷およびR¹⁸）または（R¹⁷およびR¹⁹）基は、それらが結合している1個または複数のヘテロ原子と環、具体的には、ヘテロシクリル、ヘテロシクレニル、ヘテロアリール、アリールヘテロシクリル、アリールヘテロシクレニル、ヘテロアリールヘテロシクリル、ヘテロアリールヘテロシクレニル、ヘテロシクリルヘテロアリールまたはヘテロシクレニルヘテロアリールを形成し、ここで、これらの環の各々は、今度はハロゲン、シアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルおよびオキソからなる群のm個の基によって置換されており、
mは、0、1、2、3、4または5を表し、
nは、0、1または2を表し、
sは、0、1、2、3、4、5、6、7、8、9、10または11を表す）
である。 Preference is given to compounds of formula (I)

(In the formula,
X represents C(R ¹³ )(R ¹⁴ ),
R ¹ represents (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl or heterocyclyl, where these three groups are respectively halogen, (C 1 -C 6 )-cycloalkyl, (C ₃ -C ₆ )-cycloalkyl or )-alkyl and halo-(C ₁ -C ₆ )-alkyl, where cycloalkyl, cycloalkenyl and heterocyclyl each independently have n oxo groups. ,
R ² is hydroxy, (C ₁ -C ₆ )-alkoxy, (C ₂ -C ₆ )-alkenyloxy, (C ₂ -C ₆ )-alkynyloxy, (C ₁ -C ₆ )-haloalkoxy, ( C ₂ -C ₆ )-haloalkenyloxy, (C ₂ -C ₆ )-haloalkynyloxy, where the latter six groups are cyano, R ⁸ (O)C, R ⁸ O( O)C, ( ^R8 ) ₂ N(O)C, ^R8 ( ^R8O )N(O)C, ( ^R8 ) _2N ( ^R8 )N(O)C, ^R8O , ^R8 substituted by groups of the group consisting of (O)CO, ^R9 (O) _2SO , ( ^R8 ) _2N , ^R9 (O) _nS , phenyl, heteroaryl and heterocyclyl, where these The latter three groups are respectively nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ substituted by m groups of the group consisting of N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl, where (C ₃ -C ₆ )-cycloalkyl and heterocyclyl are Each independently has n oxo groups, or
or
R ² represents (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-cycloalkenyloxy, phenyloxy, heteroaryloxy or heterocyclyloxy, in which each of these five above-mentioned groups , halogen, cyano, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ - C ₆ )-cycloalkenyl, halo-(C ₃ -C ₆ )-cycloalkyl, halo-(C ₃ -C ₆ )-cycloalkenyl, R ⁸ (O)C, R ⁸ O(O)C, (R ⁸ ) ₂ N(O)C, ^R8 ( ^R8O )N(O)C, (R8) _2N ( ^R8 )N(O)C, ^R8O , ^{R8 (} O)CO, R ⁹ (O) ₂ SO, (R ⁸ ) ₂ N, R ⁹ (O) _n S, phenyl, heteroaryl and heterocyclyl, substituted by s groups,
Here, these latter three groups are respectively nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )- Cycloalkyl, ^R10O (O)C, ( ^{R10 )} _2N (O)C, R10O, ( ^R10 ) _2N , ^R11 (O) _nS , ^R10O (O) _2S , (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl, where (C ₃ -C ₆ )-cyclo Alkoxy, (C ₃ -C ₆ )-cycloalkyl and heterocyclyl each independently have n oxo groups,
or
R ² is (R ⁸ ) ₂ N, R ⁸ (O) C (R ⁸ ) N, R ⁹ O (O) C (R ⁸ ) N, (R ⁸ ) ₂ N (O) C (R ⁸ ) N, R ⁹ (O) ₂ S (R ⁸ ) N, R ⁸ O (O) ₂ S (R ⁸ ) N, (R ⁸ ) ₂ N (O) ₂ S (R ⁸ ) N,
or
R ² represents R ⁸ (R ⁸ O)N or
R ² represents (R ¹⁷ )(R ¹⁸ )N(R ¹⁹ )N, or
or
R ² represents R ¹⁷ R ¹⁸ C=N-(R ¹⁹ )N-,
R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen, nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, halo-(C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkyl )-cycloalkyl-(C ₁ -C ₆ )-alkyl, halo-(C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, R ⁸ (O)C, R ⁸ (R ⁸ ON=)C, R ⁸ O(O)C, (R ⁸ ) ₂ N(O)C, R ⁸ O, (R ⁸ ) ₂ N, R ⁸ (O)C(R ⁸ )N, R ⁹ ( O) ₂ S (R ⁸ ) N, R ⁹ O (O) C (R ⁸ ) N, (R ⁸ ) ₂ N (O) C (R ⁸ ) N, R ⁹ (O) _n S, R ⁸ O (O) ₂ S, (R ⁸ ) ₂ N(O) ₂ S, (R ¹² O) ₂ (O) P, R ⁸ (O) C-(C ₁ to C ₆ )-alkyl, R ⁸ O( O) C-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O)C-(C ₁ to C ₆ )-alkyl, NC-(C ₁ to C ₆ )-alkyl, R ⁸ O -(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N-(C ₁ to C ₆ )-alkyl, R ⁸ (O)C(R ⁸ )N-(C ₁ to C ₆ )-alkyl, R ⁹ (O) ₂ S(R ⁸ )N-(C ₁ to C ₆ )-alkyl, R ⁹ O(O)C(R ⁸ )N-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O)C(R ⁸ )N-(C ₁ to C ₆ )-alkyl, R ⁹ (O) _n S-(C ₁ to C ₆ )-alkyl, R ⁸ O(O) ₂ S-( C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O) ₂ S-(C ₁ to C ₆ )-alkyl, (R ¹² O) ₂ (O)P-(C ₁ to C ₆ )- represents alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, where , these latter six groups are respectively nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, R ⁸ O, (R ⁸ ) ₂ N , R ⁹ (O) _n S, R ⁸ O(O) ₂ S, (R ⁸ ) ₂ N(O) ₂ S and R ⁸ O-(C ₁ -C ₆ )-alkyl. substituted by a group, where the heterocyclyl has n oxo groups,
R ⁸ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-( C ₁ to C ₆ )-alkyl, (C ₃ to C ₆ )-cycloalkyl-(C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, phenyl, phenyl-(C ₁ to C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl-O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl, where these latter nine groups are respectively nitro, halogen, ( C ₁ to C ₆ )-alkyl, halo-(C ₁ to C ₆ )-alkyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N , R ¹¹ (O) _n S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl, where the heterocyclyl has n oxo groups,
or
The two R ⁸ groups are linked to one or more heteroatoms and rings to which they are attached, specifically heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylhetero form cyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn represents halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, ( R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl and oxo is substituted by m groups of the group consisting of
R ⁹ is (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-(C ₁ ~C ₆ )-Alkyl, (C ₃ ~C ₆ )-Cycloalkyl-(C ₁ ~C ₆ )-Alkyl-O-(C ₁ ~C ₆ )-Alkyl, Phenyl, Phenyl-(C ₁ ~C _{6 )} )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl -O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl, where these latter nine groups are respectively nitro, halogen, (C _{1 -C 6} )-alkyl; C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl, wherein the heterocyclyl has n oxo groups;
R ¹⁰ represents hydrogen or (C ₁ -C ₆ )-alkyl;
R ¹¹ represents (C ₁ -C ₆ )-alkyl,
R ¹² represents (C1-C4)-alkyl,
R ¹³ and R ¹⁴ are each independently hydrogen, (C ₁ -C ₆ )-alkyl, hydroxy, (C ₁ -C ₆ )-alkoxy, (R ⁸ ) ₂ N, halo-(C ₁ -C ₆ )-alkoxy, halogen, halo-(C ₁ -C ₆ )-alkyl, cyano, R ⁸ O(O)C or (R ⁸ ) ₂ N(O)C,
or
R ¹³ and R ¹⁴ together with the carbon atom to which they are attached form a (C ₃ -C ₈ )-cycloalkyl group;
R ¹⁵ and R ¹⁶ each independently represent (C ₁ -C ₆ )-alkyl, phenyl, (C ₃ -C ₆ )-cycloalkyl, heteroaryl or heterocyclyl;
R ¹⁷ , R ¹⁸ and R ¹⁹ are independently R ⁸ or R ⁹ S(O) ₂ , (R ⁸ ) ₂ NS(O) ₂ , R ⁸ OS(O) ₂ , R ⁹ C(O), (R ⁸ ) ₂ NC(O), (R ⁸ ) ₂ NC(S), R ⁸ OC(O), R ⁸ OC(O) C(O), (R ⁸ ) ₂ NC(O) C(O ) or (R ¹⁷ and R ¹⁸ ) or (R ¹⁷ and R ¹⁹ ) groups represent one or more heteroatoms and rings to which they are attached, in particular heterocyclyl, heterocyclenyl, hetero aryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn represents halogen, cyano, ( C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C , (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ substituted by m groups of the group consisting of S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl and oxo;
m represents 0, 1, 2, 3, 4 or 5;
n represents 0, 1 or 2;
s represents 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11)
It is.

（式中、
Xは、C（R¹³）（R¹⁴）を表し、
R¹は、（C₃～C₆）－シクロアルキルを表し、ここで、このシクロアルキル基は、ハロゲン、（C₁～C₆）－アルキルおよびハロ－（C₁～C₆）－アルキルからなる群の基により置換されており、
R²は、ヒドロキシ、（C₁～C₆）－アルコキシ、（C₁～C₆）－ハロアルコキシ、（C₂～C₆）－アルケニルオキシ、（C₂～C₆）－ハロアルケニルオキシ、（C₂～C₆）－アルキニルオキシを表し、ここで、これらの後の5つの基は、各々、R⁸（O）C、R⁸O（O）C、（R⁸）₂N（O）C、R⁸（R⁸O）N（O）C、（（R⁸）₂N（R⁸）N（O）C、R⁸Oおよびフェニルの群の基により置換されており、ここで、これらの最後の基は、いずれの場合にも、ニトロ、ハロゲン、シアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキルおよび（C₃～C₆）－シクロアルキルからなる群のm個の基により置換されているか、
または
R²は、（R⁸）₂N、R⁸（O）C（R⁸）N、R⁹O（O）C（R⁸）N、（R⁸）₂N（O）C（R⁸）N、R⁹（O）₂S（R⁸）N、R⁸O（O）₂S（R⁸）N、（R⁸）₂N（O）₂S（R⁸）Nを表すか、
または
R²は、R⁸（R⁸O）Nを表すか
または
R²は、（R¹⁷）（R¹⁸）N（R¹⁹）Nを表すか、
または
R²は、R¹⁷R¹⁸C＝N－（R¹⁹）N－を表し
R³、R⁴、R⁵、R⁶およびR⁷は、各々独立に、水素、ニトロ、ハロゲン、シアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、R⁸O（O）C、R⁸OまたはR⁹（O）_nSを表し、
R⁸は、水素、（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、フェニル、フェニル－（C₁～C₆）－アルキル、ヘテロアリール、ヘテロアリール－（C₁～C₆）－アルキル、ヘテロシクリル、ヘテロシクリル－（C₁～C₆）－アルキル、フェニル－O－（C₁～C₆）－アルキル、ヘテロアリール－O－（C₁～C₆）－アルキルまたはヘテロシクリル－O－（C₁～C₆）－アルキルを表し、ここで、これらの後の9つの基は各々、ニトロ、ハロゲン、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nSおよびR¹⁰O－（C₁～C₆）－アルキルからなる群のm個の基により置換されており、ここでヘテロシクリルはn個のオキソ基を有するか、
または
2つのR⁸基は、それらが結合している1個または複数のヘテロ原子と環、具体的には、ヘテロシクリル、ヘテロシクレニル、ヘテロアリール、アリールヘテロシクリル、アリールヘテロシクレニル、ヘテロアリールヘテロシクリル、ヘテロアリールヘテロシクレニル、ヘテロシクリルヘテロアリールまたはヘテロシクレニルヘテロアリールを形成し、ここで、これらの環の各々は、今度はニトロ、ハロゲン、シアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルおよびオキソからなる群のm個の基によって置換されており、
R⁹は、（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、フェニル、フェニル－（C₁～C₆）－アルキル、ヘテロアリール、ヘテロアリール－（C₁～C₆）－アルキル、ヘテロシクリル、ヘテロシクリル－（C₁～C₆）－アルキル、フェニル－O－（C₁～C₆）－アルキル、ヘテロアリール－O－（C₁～C₆）－アルキルまたはヘテロシクリル－O－（C₁～C₆）－アルキルを表し、ここで、これらの後の9つの基は各々、ニトロ、ハロゲン、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nSおよびR¹⁰O－（C₁～C₆）－アルキルからなる群のm個の基により置換されており、ここでヘテロシクリルはn個のオキソ基を有し、
R¹⁰は、水素または（C₁～C₆）－アルキルを表し、
R¹¹は、（C₁～C₆）－アルキルを表し、
R¹²は、（C₁～C₄）－アルキルを表し、
R¹³およびR¹⁴は、各々独立に、水素、（C₁～C₆）－アルキル、シアノ、R⁸O（O）Cまたは（R⁸）₂N（O）Cを表し、
R¹⁵およびR¹⁶は、各々独立に、（C₁～C₆）－アルキル、フェニル、（C₃～C₆）－シクロアルキル、ヘテロアリールまたはヘテロシクリルを表し、
R¹⁷、R¹⁸およびR¹⁹は、独立に、R⁸またはR⁹S（O）₂、（R⁸）₂NS（O）₂、R⁸OS（O）₂、R⁹C（O）、（R⁸）₂NC（O）、（R⁸）₂NC（S）、R⁸OC（O）、R⁸OC（O）C（O）、（R⁸）₂NC（O）C（O）を表すか、
または
あるいは（R¹⁷およびR¹⁸）または（R¹⁷およびR¹⁹）基は、それらが結合している1個または複数のヘテロ原子と環、具体的には、ヘテロシクリル、ヘテロシクレニル、ヘテロアリール、アリールヘテロシクリル、アリールヘテロシクレニル、ヘテロアリールヘテロシクリル、ヘテロアリールヘテロシクレニル、ヘテロシクリルヘテロアリールまたはヘテロシクレニルヘテロアリールを形成し、ここで、これらの環の各々は、今度はニトロ、ハロゲン、シアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルおよびオキソからなる群のm個の基によって置換されており、
mは、0または1、2、3、4または5を表し、
nは、0、1または2を表し、
sは、0、1、2、3、4、5、6、7、8、9、10または11を表す）
である。 Particularly preferred are compounds of formula (I)

(In the formula,
X represents C(R ¹³ )(R ¹⁴ ),
R ¹ represents (C ₃ -C ₆ )-cycloalkyl, where the cycloalkyl group is selected from halogen, (C ₁ -C ₆ )-alkyl and halo-(C ₁ -C ₆ )-alkyl. is substituted with a group of
R ² is hydroxy, (C ₁ -C ₆ )-alkoxy, (C ₁ -C ₆ )-haloalkoxy, (C ₂ -C ₆ )-alkenyloxy, (C ₂ -C ₆ )-haloalkenyloxy, represents (C ₂ -C ₆ )-alkynyloxy, where these latter five groups are R ⁸ (O)C, R ⁸ O(O)C, (R ⁸ ) ₂ N(O )C, ^R8 ( ^R8O )N(O)C, (( ^R8 ) _2N ( ^R8 )N(O)C, ^R8O and phenyl, where , these last groups are in each case nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl and (C ₃ -C ₆ )- substituted by m groups of the group consisting of cycloalkyl,
or
R ² is (R ⁸ ) ₂ N, R ⁸ (O) C (R ⁸ ) N, R ⁹ O (O) C (R ⁸ ) N, (R ⁸ ) ₂ N (O) C (R ⁸ ) N, R ⁹ (O) ₂ S (R ⁸ ) N, R ⁸ O (O) ₂ S (R ⁸ ) N, (R ⁸ ) ₂ N (O) ₂ S (R ⁸ ) N,
or
R ² represents R ⁸ (R ⁸ O)N or
R ² represents (R ¹⁷ )(R ¹⁸ )N(R ¹⁹ )N, or
or
R ² represents R ¹⁷ R ¹⁸ C=N-(R ¹⁹ )N-
R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen, nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, R ⁸ O(O)C, R ⁸ O or R ⁹ (O) _n S;
R ⁸ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-( C ₁ to C ₆ )-alkyl, (C ₃ to C ₆ )-cycloalkyl-(C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, phenyl, phenyl-(C ₁ to C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, represents heteroaryl-O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl, where these latter nine groups are each nitro, halogen, (C ₁ to C ₆ )-alkyl, halo-(C ₁ to C ₆ )-alkyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, substituted by m groups of the group consisting of R ¹¹ (O) _n S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl, where the heterocyclyl has n oxo groups,
or
The two R ⁸ groups are linked to one or more heteroatoms and rings to which they are attached, specifically heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylhetero form cyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn represents nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ - C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O , (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl and oxo,
R ⁹ is (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-(C ₁ ~C ₆ )-Alkyl, (C ₃ ~C ₆ )-Cycloalkyl-(C ₁ ~C ₆ )-Alkyl-O-(C ₁ ~C ₆ )-Alkyl, Phenyl, Phenyl-(C ₁ ~C _{6 )} )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl -O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl, where these latter nine groups are respectively nitro, halogen, (C _{1 -C 6} )-alkyl; C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl, wherein the heterocyclyl has n oxo groups;
R ¹⁰ represents hydrogen or (C ₁ -C ₆ )-alkyl;
R ¹¹ represents (C ₁ -C ₆ )-alkyl,
R ¹² represents (C ₁ -C ₄ )-alkyl,
R ¹³ and R ¹⁴ each independently represent hydrogen, (C ₁ -C ₆ )-alkyl, cyano, R ⁸ O(O)C or (R ⁸ ) ₂ N(O)C,
R ¹⁵ and R ¹⁶ each independently represent (C ₁ -C ₆ )-alkyl, phenyl, (C ₃ -C ₆ )-cycloalkyl, heteroaryl or heterocyclyl;
R ¹⁷ , R ¹⁸ and R ¹⁹ are independently R ⁸ or R ⁹ S(O) ₂ , (R ⁸ ) ₂ NS(O) ₂ , R ⁸ OS(O) ₂ , R ⁹ C(O), (R ⁸ ) ₂ NC(O), (R ⁸ ) ₂ NC(S), R ⁸ OC(O), R ⁸ OC(O) C(O), (R ⁸ ) ₂ NC(O) C(O ) or
or Alternatively, the (R ¹⁷ and R ¹⁸ ) or (R ¹⁷ and R ¹⁹ ) groups include one or more heteroatoms and rings to which they are attached, in particular heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl. , arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn represents nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, ( R ¹⁰ ) ₂ N(O) C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and substituted by m groups of the group consisting of R ¹⁰ O-(C ₁ -C ₆ )-alkyl and oxo;
m represents 0 or 1, 2, 3, 4 or 5;
n represents 0, 1 or 2;
s represents 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11)
It is.

（式中、
Xは、CH₂を表し、
R¹は、シクロプロピルを表し、ここで、シクロプロピル基は、ハロゲン、（C₁～C₆）－アルキルおよびハロ－（C₁～C₆）－アルキルからなる群の基により置換されており、
R²は、ヒドロキシ、（C₁～C₆）－アルコキシ、（C₁～C₆）－ハロアルコキシ、（C₂～C₆）－アルケニルオキシ、（C₂～C₆）－ハロアルケニルオキシ、（C₂～C₆）－アルキニルオキシを表すか、
または
R²は、（R⁸）₂N、R⁸（O）C（R⁸）N、R⁹O（O）C（R⁸）N、（R⁸）₂N（O）C（R⁸）N、R⁹（O）₂S（R⁸）N、R⁸O（O）₂S（R⁸）N、（R⁸）₂N（O）₂S（R⁸）Nを表すか、
または
R²は、R⁸（R⁸O）Nを表すか
または
R²は、（R¹⁷）（R¹⁸）N（R¹⁹）Nを表すか、
または
R²は、R¹⁷R¹⁸C＝N－（R¹⁹）N－を表し
または
あるいは（R¹⁷およびR¹⁸）または（R¹⁷およびR¹⁹）基は、それらが結合している1個または複数のヘテロ原子と環、具体的には、ヘテロシクリル、ヘテロシクレニル、ヘテロアリール、アリールヘテロシクリル、アリールヘテロシクレニル、ヘテロアリールヘテロシクリル、ヘテロアリールヘテロシクレニル、ヘテロシクリルヘテロアリールまたはヘテロシクレニルヘテロアリールを形成し、ここで、これらの環の各々は、今度はニトロ、ハロゲン、シアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルおよびオキソからなる群のm個の基によって置換されており、
R³は、シアノ、フッ素、塩素、臭素、メチル、エチル、トリフルオロメチル、ジフルオロメチル、シクロプロピル、ヒドロキシカルボニル、メトキシカルボニル、エトキシカルボニル、メトキシ、エトキシ、メチルスルファニル、メチルスルフィニルまたはメチルスルホニルを表し、
R⁴、R⁵、R⁶およびR⁷は、各々独立に、水素、シアノ、フッ素、塩素、臭素、メチル、エチル、トリフルオロメチル、ジフルオロメチル、シクロプロピル、ヒドロキシカルボニル、メトキシカルボニル、エトキシカルボニル、メトキシ、エトキシ、メチルスルファニル、メチルスルフィニルまたはメチルスルホニルを表し、
R⁸は、水素、（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、フェニル、フェニル－（C₁～C₆）－アルキル、ヘテロアリール、ヘテロアリール－（C₁～C₆）－アルキル、ヘテロシクリル、ヘテロシクリル－（C₁～C₆）－アルキル、フェニル－O－（C₁～C₆）－アルキル、ヘテロアリール－O－（C₁～C₆）－アルキルまたはヘテロシクリル－O－（C₁～C₆）－アルキルを表し、ここで、これらの後の9つの基は各々、ニトロ、ハロゲン、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nSおよびR¹⁰O－（C₁～C₆）－アルキルからなる群のm個の基により置換されており、ここでヘテロシクリルはn個のオキソ基を有するか、
または
2つのR⁸基は、それらが結合している1個または複数のヘテロ原子と環、具体的には、ヘテロシクリル、ヘテロシクレニル、ヘテロアリール、アリールヘテロシクリル、アリールヘテロシクレニル、ヘテロアリールヘテロシクリル、ヘテロアリールヘテロシクレニル、ヘテロシクリルヘテロアリールまたはヘテロシクレニルヘテロアリールを形成し、ここで、これらの環の各々は、今度はニトロ、ハロゲン、シアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルおよびオキソからなる群のm個の基によって置換されており、
R⁹は、（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル、（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル－（C₁～C₆）－アルキル－O－（C₁～C₆）－アルキル、フェニル、フェニル－（C₁～C₆）－アルキル、ヘテロアリール、ヘテロアリール－（C₁～C₆）－アルキル、ヘテロシクリル、ヘテロシクリル－（C₁～C₆）－アルキル、フェニル－O－（C₁～C₆）－アルキル、ヘテロアリール－O－（C₁～C₆）－アルキルまたはヘテロシクリル－O－（C₁～C₆）－アルキルを表し、ここで、これらの後の9つの基は各々、ニトロ、ハロゲン、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nSおよびR¹⁰O－（C₁～C₆）－アルキルからなる群のm個の基により置換されており、ここでヘテロシクリルはn個のオキソ基を有し、
R¹⁰は、水素または（C₁～C₆）－アルキルを表し、
R¹¹は、（C₁～C₆）－アルキルを表し、
R¹²は、（C₁～C₄）－アルキルを表し、
R¹³およびR¹⁴は、各々独立に、水素、（C₁～C₆）－アルキル、シアノ、R⁸O（O）Cまたは（R⁸）₂N（O）Cを表し、
R¹⁵およびR¹⁶は、各々独立に、（C₁～C₆）－アルキル、フェニル、（C₃～C₆）－シクロアルキル、ヘテロアリールまたはヘテロシクリルを表し、
R¹⁷、R¹⁸およびR¹⁹は、独立に、R⁸またはR⁹S（O）₂、（R⁸）₂NS（O）₂、R⁸OS（O）₂、R⁹C（O）、（R⁸）₂NC（O）、（R⁸）₂NC（S）、R⁸OC（O）、R⁸OC（O）C（O）、（R⁸）₂NC（O）C（O）を表すか、
または
（R¹⁷およびR¹⁸）または（R¹⁷およびR¹⁹）基は、それらが結合している1個または複数のヘテロ原子と環、具体的には、ヘテロシクリル、ヘテロシクレニル、ヘテロアリール、アリールヘテロシクリル、アリールヘテロシクレニル、ヘテロアリールヘテロシクリル、ヘテロアリールヘテロシクレニル、ヘテロシクリルヘテロアリールまたはヘテロシクレニルヘテロアリールを形成し、ここで、これらの環の各々は、今度はハロゲン、シアノ、（C₁～C₆）－アルキル、ハロ－（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₃～C₆）－シクロアルケニル、R¹⁰O（O）C、（R¹⁰）₂N（O）C、R¹⁰O、（R¹⁰）₂N、R¹¹（O）_nS、R¹⁰O（O）₂S、（R¹⁰）₂N（O）₂SおよびR¹⁰O－（C₁～C₆）－アルキルおよびオキソからなる群のm個の基によって置換されており、
mは、0、1、2または3を表し、
nは、0、1または2を表し、
sは、0、1、2、3、4または5を表す）
である。 Very particular preference is given to compounds of formula (I)

(In the formula,
X represents _CH2 ;
R ¹ represents cyclopropyl, where the cyclopropyl group is substituted by a group consisting of halogen, (C ₁ -C ₆ )-alkyl and halo-(C ₁ -C ₆ )-alkyl. ,
R ² is hydroxy, (C ₁ -C ₆ )-alkoxy, (C ₁ -C ₆ )-haloalkoxy, (C ₂ -C ₆ )-alkenyloxy, (C ₂ -C ₆ )-haloalkenyloxy, (C ₂ -C ₆ )-alkynyloxy,
or
R ² is (R ⁸ ) ₂ N, R ⁸ (O) C (R ⁸ ) N, R ⁹ O (O) C (R ⁸ ) N, (R ⁸ ) ₂ N (O) C (R ⁸ ) N, R ⁹ (O) ₂ S (R ⁸ ) N, R ⁸ O (O) ₂ S (R ⁸ ) N, (R ⁸ ) ₂ N (O) ₂ S (R ⁸ ) N,
or
R ² represents R ⁸ (R ⁸ O)N or
R ² represents (R ¹⁷ )(R ¹⁸ )N(R ¹⁹ )N, or
or
R ² represents R ¹⁷ R ¹⁸ C=N-(R ¹⁹ )N- or alternatively (R ¹⁷ and R ¹⁸ ) or (R ¹⁷ and R ¹⁹ ) groups and a ring, specifically forming heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where and each of these rings is in turn nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ - C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R substituted by m groups of the group consisting of ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl and oxo,
R ³ represents cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl;
R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, represents methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl,
R ⁸ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-( C ₁ to C ₆ )-alkyl, (C ₃ to C ₆ )-cycloalkyl-(C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, phenyl, phenyl-(C ₁ to C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, represents heteroaryl-O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl, where these latter nine groups are each nitro, halogen, (C ₁ to C ₆ )-alkyl, halo-(C ₁ to C ₆ )-alkyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, substituted by m groups of the group consisting of R ¹¹ (O) _n S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl, where the heterocyclyl has n oxo groups,
or
The two R ⁸ groups are linked to one or more heteroatoms and rings to which they are attached, specifically heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylhetero form cyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn represents nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ - C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O , (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl and oxo,
R ⁹ is (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-(C ₁ ~C ₆ )-Alkyl, (C ₃ ~C ₆ )-Cycloalkyl-(C ₁ ~C ₆ )-Alkyl-O-(C ₁ ~C ₆ )-Alkyl, Phenyl, Phenyl-(C ₁ ~C _{6 )} )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl -O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl, where these latter nine groups are respectively nitro, halogen, (C _{1 -C 6} )-alkyl; C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl, wherein the heterocyclyl has n oxo groups;
R ¹⁰ represents hydrogen or (C ₁ -C ₆ )-alkyl;
R ¹¹ represents (C ₁ -C ₆ )-alkyl,
R ¹² represents (C ₁ -C ₄ )-alkyl,
R ¹³ and R ¹⁴ each independently represent hydrogen, (C ₁ -C ₆ )-alkyl, cyano, R ⁸ O(O)C or (R ⁸ ) ₂ N(O)C,
R ¹⁵ and R ¹⁶ each independently represent (C ₁ -C ₆ )-alkyl, phenyl, (C ₃ -C ₆ )-cycloalkyl, heteroaryl or heterocyclyl;
R ¹⁷ , R ¹⁸ and R ¹⁹ are independently R ⁸ or R ⁹ S(O) ₂ , (R ⁸ ) ₂ NS(O) ₂ , R ⁸ OS(O) ₂ , R ⁹ C(O), (R ⁸ ) ₂ NC(O), (R ⁸ ) ₂ NC(S), R ⁸ OC(O), R ⁸ OC(O) C(O), (R ⁸ ) ₂ NC(O) C(O ) or
or (R ¹⁷ and R ¹⁸ ) or (R ¹⁷ and R ¹⁹ ) groups include one or more heteroatoms and rings to which they are attached, in particular heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, form arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn represents halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O substituted by m groups of the group consisting of -(C ₁ -C ₆ )-alkyl and oxo,
m represents 0, 1, 2 or 3;
n represents 0, 1 or 2;
s represents 0, 1, 2, 3, 4 or 5)
It is.

（式中、
Xは、CH₂を表し、
R¹は、シクロプロピルを表し、ここでシクロプロピルアルキル基は、ハロゲン、（C₁～C₆）－アルキルおよびハロ－（C₁～C₆）－アルキルからなる群の基により置換されており、
R²は、ヒドロキシ、（C₁～C₆）－アルコキシ、（C₁～C₆）－ハロアルコキシ、（C₂～C₆）－アルケニルオキシ、（C₂～C₆）－ハロアルケニルオキシ、（C₂～C₆）－アルキニルオキシを表し、
R³は、シアノ、フッ素、塩素、臭素、メチル、エチル、トリフルオロメチル、ジフルオロメチル、シクロプロピル、ヒドロキシカルボニル、メトキシカルボニル、エトキシカルボニル、メトキシ、エトキシ、メチルスルファニル、メチルスルフィニルまたはメチルスルホニルを表し、
R⁴、R⁵、R⁶およびR⁷は、各々独立に、水素、シアノ、フッ素、塩素、臭素、メチル、エチル、トリフルオロメチル、ジフルオロメチル、シクロプロピル、ヒドロキシカルボニル、メトキシカルボニル、エトキシカルボニル、メトキシ、エトキシ、メチルスルファニル、メチルスルフィニルまたはメチルスルホニルを表し、
mは、0、1、2または3を表し、
nは、0、1または2を表し、
sは、0、1、2、3、4または5を表す）
である。 Highly preferred are compounds of formula (I)

(In the formula,
X represents _CH2 ;
R ¹ represents cyclopropyl, where the cyclopropylalkyl group is substituted by a group consisting of halogen, (C ₁ -C ₆ )-alkyl and halo-(C ₁ -C ₆ )-alkyl. ,
R ² is hydroxy, (C ₁ -C ₆ )-alkoxy, (C ₁ -C ₆ )-haloalkoxy, (C ₂ -C ₆ )-alkenyloxy, (C ₂ -C ₆ )-haloalkenyloxy, (C ₂ -C ₆ )-alkynyloxy,
R ³ represents cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl;
R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, represents methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl,
m represents 0, 1, 2 or 3;
n represents 0, 1 or 2;
s represents 0, 1, 2, 3, 4 or 5)
It is.

In the context of the present invention, the substituents X, Z, ^R1 , ^R2 , ^R3 , ^R4 , R5 ^{, R6} , ^R7 , ^R8 , ^R9 , ^R10 , ^R11 , ^R12 , ^R13 , R ¹⁴ , R ¹⁵ , R ¹⁶ and the definitions of the indices n, m and s can be combined in any way. This means that, for example, the substituent R ¹ has a preferred definition and the substituents R ² to R ⁷ have a general definition, or the substituent R ¹ has a preferred definition and the substituent R ¹⁰ is meant to cover compounds of general formula (I) in which have a particularly preferred or very particularly preferred definition and the remaining substituents have the general definition.

The compounds of formula (I) according to the invention listed in Tables 1 to 4 below are likewise very particularly preferred. The abbreviations of chemical groups used therein follow the nomenclature known to those skilled in the art and mean, for example:
Bu=butyl Et=ethyl Me=methyl
Ph=phenyl Pr=propyl c=cyclo
i = iso
Bn=benzyl Ac=acetyl

NMR data for selected examples
NMR Peak List Method The 1H NMR data of selected examples are referred to in the form of 1H NMR peak list. For each signal peak, first list the δ value (ppm) and then the signal intensity in parentheses. The δ value/signal intensity number pairs for different signal peaks are listed, separated from each other by semicolons.

Therefore, the peak list for a given example takes the following form:
δ ₁ (Intensity ₁ ); δ ₂ (Intensity ₂ );……. ．． ;δ _i (intensity _i );……. ．． ; δ _n (intensity _n ).

The intensity of the sharp signal correlates with the signal height (cm) of the printed example of the NMR spectrum, indicating the exact ratio of signal intensities. In the case of a broad signal, several peaks or the center of the signal and its intensity can be shown compared to the strongest signal in the spectrum.

For the calibration of the chemical shifts of the 1H NMR spectra, the chemical shifts of the solvent are used, in the case of spectra measured with tetramethylsilane and/or especially DMSO. Therefore, although a tetramethylsilane peak can occur in the NMR peak list, it does not need to occur.

The list of 1H NMR peaks is similar to a conventional 1H NMR printout, so it usually includes all peaks listed in conventional NMR interpretation.

Furthermore, like conventional 1H NMR printouts, these may show solvent signals, signals of stereoisomers of the target compound, which also form part of the subject of the invention, and/or impurity peaks.

When reporting compound signals in the δ range of solvent and/or water, the list of 1H NMR peaks shows the usual solvent peaks, e.g., the peak of DMSO in DMSO- _D6 and the peak of water, which are usually averaged. Has high strength.

Stereoisomeric peaks and/or impurity peaks of the target compound typically have lower intensities on average than the peaks of the target compound (eg, having greater than 90% purity).

Such stereoisomers and/or impurities may be inherent to a particular method of preparation. Therefore, the peak can be useful in identifying the reproduction of the preparation method with reference to the "by-product fingerprint".

An expert who calculates the target compound peak by known methods (MestreC, ACD simulations, but also using empirically evaluated expectations) calculates the target compound peak, if necessary, possibly using further intensity filters. can be isolated. This isolation will be similar to relevant peak picking in conventional 1H NMR interpretation.

Further details about 1H NMR can be found in Research Disclosure Database Number 564025.

I-137: ^1H -NMR (400.6 MHz, CDCl3):
δ = 15.9527 (1.5); 8.2222 (15.2); 7.5255 (2.5); 7.5215 (4.0); 7.5191 (1.9); 7.5079 (2.8); 7.5060 (3.1); 7.5029 (3.9); 7.4135 (1.4); 7.4087 (1.9); 7.3950 (4.0) ;7.3901(3.9);7.3767(6.2);7.3717(4.4);7.3710(4.1);7.3584(4.6);7.3545( 4.1); 7.3398 (1.8); 7.3359 (1.5); 7.2711 (0.6); 7.2686 (0.8); 7.2678 (0.9); 7.2670 (1.0); 7.2661 (1.1); 7.2607 (273.0); 7.2564 (7.1); 7.2555 (6.5); 7.2539 (7 .1); 7.2532 (6.7); 7.2516 (3.5); 7.2492 (4.7); 7.2473 (4.0); 7.2452 (1.4); 7 .2436 (1.1); 7.2420 (0.9); 7.2404 (1.0); 7.2396 (1.0); 7.2388 (1.1); 7.2356 (4. 4); 7.2307 (3.1); 6.9970 (2.3); 6.1433 (16.0); 5.4241 (1.0); 2.2220 (0.6); 2. 2101 (1.4); 2.2019 (1.4); 2.1961 (0.7); 2.1903 (2.5); 2.1814 (1.0); 2.1780 (1.5 ); 2.1699 (1.6); 2.1579 (0.8); 1.5509 (4.0); 1.3331 (0.5); 1.3197 (1.4); 1.3109 (1.4); 1.3038 (2.7); 1.2989 (3.3); 1.2951 (3.2); 1.2917 (2.9); 1.2891 (2.6) ;1.2837(2.7);1.2729(0.8);1.2569(1.8);1.2544(2.2);1.2447(4.3);1.2381( 2.5); 1.2342 (1.8); 1.2247 (4.0); 1.2176 (2.8); 1.2108 (1.5); 1.2039 (0.7); 0.0080 (4.3); -0.0002 (170.5); -0.0085 (5.6); -0.0133 (0.9)
I-139: ^1H -NMR (400.6 MHz, CDCl3):
δ = 8.0295 (6.2); 7.4951 (1.2); 7.4905 (1.6); 7.4782 (1.1); 7.4757 (1.2); 7.4721 (1.6); 7.3856 (0.6); 7.3805 (0.8); 7.3671 (1.7); 7.3619 (1.9); 7.3532 (1.4) ;7.3493(1.7);7.3477(1.7);7.3429(1.6);7.3349(1.9);7.3308(1.8);7.3164( 0.8); 7.3123 (0.6); 7.2687 (4.0); 7.2566 (1.7); 7.2522 (1.2); 7.2498 (1.1); 7.2392 (1.5); 7.2335 (1.0); 5.3291 (7.2); 4.1305 (1.0); 4.1127 (1.1); 3.1090 (2 .3); 3.1043 (16.0); 2.9565 (2.4); 2.9519 (14.7); 2.1336 (0.6); 2.1252 (0.6); 2 .1136 (1.2); 2.1016 (0.7); 2.0932 (0.7); 2.0454 (5.1); 1.3163 (0.5); 1.3102 (1. 2); 1.3041 (2.1); 1.3002 (1.1); 1.2982 (1.0); 1.2960 (1.2); 1.2925 (1.7); 1. 2843 (0.9); 1.2769 (1.6); 1.2591 (3.3); 1.2550 (0.6); 1.2413 (1.6); 1.2377 (0.7 ); 1.2353 (0.6); 1.2282 (1.6); 1.2213 (1.1); 1.2170 (1.0); 1.2083 (1.8); 1.2010 (1.2); 1.1973 (0.7); -0.0002 (2.9)
I-146: ^1H -NMR (400.6 MHz, CDCl3):
δ = 15.8625 (1.3); 8.3673 (1.3); 8.0941 (14.7); 7.4950 (2.9); 7.4896 (3.2); 7.4786 (2.3); 7.4755 (2.6); 7.4718 (4.1); 7.3803 (1.1); 7.3751 (1.5); 7.3698 (0.5) ;7.3618(3.6);7.3565(4.3);7.3511(3.9);7.3449(6.4);7.3378(3.6);7.3331( 4.3); 7.3287 (4.0); 7.3146 (1.6); 7.3102 (1.1); 7.2790 (2.9); 7.2605 (4.3); 7.2557 (2.7); 7.2526 (2.3); 7.2434 (2.9); 7.2372 (2.6); 5.6792 (16.0); 4.1108 (0 .6); 3.7816 (0.7); 3.7689 (1.5); 3.7525 (3.3); 3.7464 (1.6); 3.7347 (2.5); 3 .7309 (2.8); 3.7140 (1.9); 3.7017 (1.0); 3.5133 (4.3); 3.4959 (6.8); 3.4797 (3. 5); 2.1794 (0.7); 2.1675 (1.4); 2.1591 (1.5); 2.1550 (0.9); 2.1475 (3.0); 2. 1385 (1.1); 2.1355 (1.6); 2.1271 (1.6); 2.1153 (0.8); 2.0437 (1.3); 1.9454 (0.5 ); 1.9390 (0.9); 1.9290 (1.2); 1.9219 (2.1); 1.9082 (3.8); 1.8927 (4.2); 1.8798 (3.1); 1.8664 (3.2); 1.8505 (3.5); 1.8365 (1.7); 1.8343 (1.8); 1.8306 (1.3) ;1.8199(0.6);1.3371(0.6);1.3079(1.6);1.3021(1.9);1.2959(3.4);1.2896( 6.0); 1.2857 (4.2); 1.2820 (4.1); 1.2780 (5.0); 1.2697 (3.8); 1.2617 (3.6); 1.2579 (3.1); 1.2434 (1.2); 1.2316 (0.8); 1.2243 (1.5); 1.2212 (1.4); 1.2149 (4 .4); 1.2080 (3.0); 1.2037 (2.5); 1.1949 (4.7); 1.1877 (3.1); 1.1840 (1.6); 1 .1777 (0.8); 1.1749 (0.8); 1.0720 (0.5); 1.0523 (0.7); 0.8973 (1.5); 0.8804 (4. 6); 0.8628 (1.9); 0.0755 (0.9); -0.0002 (2.1)
I-547: ^1H -NMR (400.6 MHz, CDCl3):
δ = 15.8263 (0.5); 7.9951 (6.1); 7.2687 (7.8); 7.2592 (1.5); 7.2527 (1.6); 7.2498 (1.4); 7.2381 (1.5); 7.2349 (1.5); 7.2318 (1.7); 7.2284 (1.8); 7.2135 (1.6) ;7.0931(1.1);7.0867(1.0);7.0733(1.2);7.0720(1.1);7.0668(1.1);7.0656( 0.9); 7.0521 (0.8); 7.0456 (0.8); 5.3008 (11.2); 3.1314 (1.4); 3.1070 (16.0); 2.9594 (14.9); 2.1246 (0.6); 2.1163 (0.6); 2.1047 (1.2); 2.0926 (0.6); 2.0843 (0 .7); 1.3075 (1.0); 1.3018 (2.0); 1.2991 (1.2); 1.2942 (1.3); 1.2901 (1.6); 1 .2822 (0.9); 1.2413 (0.6); 1.2379 (0.5); 1.2319 (1.6); 1.2249 (1.1); 1.2210 (0. 8); 1.2184 (0.8); 1.2120 (1.7); 1.2046 (1.2); 1.2002 (0.6); -0.0002 (4.7)
I-688: ^1H -NMR (400.0 MHz, CDCl3):
δ = 8.1801 (13.8); 7.2848 (3.5); 7.2785 (3.9); 7.2614 (24.8); 7.2575 (4.4); 7.2443 (3.2); 7.2295 (2.9); 7.2229 (3.6); 7.2082 (3.5); 7.1113 (2.3); 7.1049 (2.1) ;7.0915(2.7);7.0901(2.3);7.0851(2.4);7.0837(2.0);7.0702(1.7);7.0638( 1.6); 6.1127 (16.0); 5.9049 (0.7); 5.8908 (1.5); 5.8792 (0.9); 5.8768 (0.8); 5.8652 (1.7); 5.8620 (0.9); 5.8511 (0.9); 5.8479 (1.8); 5.8363 (1.0); 5.8340 (1 .0); 5.8223 (1.9); 5.8083 (0.9); 5.2996 (3.8); 5.2561 (1.0); 5.2521 (2.6); 5 .2487 (2.7); 5.2446 (1.1); 5.2132 (0.9); 5.2092 (2.3); 5.2058 (2.4); 5.2017 (1. 0); 5.1832 (1.2); 5.1797 (3.0); 5.1764 (2.9); 5.1730 (1.0); 5.1575 (1.0); 5. 1541 (2.8); 5.1508 (2.7); 5.1474 (1.0); 3.9765 (1.6); 3.9727 (2.8); 3.9689 (1.8 ); 3.9616 (2.8); 3.9580 (4.8); 3.9545 (2.8); 3.9472 (1.7); 3.9434 (2.8); 3.9396 (1.6); 2.2232 (0.5); 2.2112 (1.2); 2.2034 (1.3); 2.1936 (1.8); 2.1917 (1.8) ;2.1827(0.9);2.1792(1.3);2.1713(1.4);2.1591(0.7);2.0464(0.7);1.3327( 3.0); 1.3181 (1.6); 1.3155 (1.7); 1.3105 (3.2); 1.3072 (3.2); 1.3040 (3.5); 1.2990 (3.3); 1.2958 (2.3); 1.2926 (2.3); 1.2846 (4.7); 1.2809 (3.2); 1.2732 (4 .2); 1.2662 (2.8); 1.2536 (5.7); 1.2461 (2.7); 1.2373 (0.7); 1.2316 (1.0); 0 .8799 (0.5); 0.0080 (0.7); -0.0002 (30.2); -0.0085 (1.1)
II-003: ^1H -NMR (400.0 MHz, CDCl3):
δ = 15.6674 (2.0); 15.4327 (0.6); 8.3695 (9.4); 8.3105 (2.1); 7.5152 (0.5); 7.5121 (1.0); 7.5071 (1.4); 7.5030 (0.9); 7.4963 (1.3); 7.4903 (4.3); 7.4859 (2.3) ;7.4798(1.4);7.4760(2.2);7.4724(4.7);7.4705(3.3);7.4661(1.2);7.4639( 1.7); 7.4597 (3.1); 7.4557 (2.1); 7.4491 (0.9); 7.4423 (2.3); 7.4331 (0.6); 7.4274 (0.5); 7.4238 (0.7); 7.3904 (0.9); 7.3865 (1.2); 7.3737 (0.5); 7.3697 (1 .0); 7.3634 (4.2); 7.3592 (4.9); 7.3537 (1.4); 7.3472 (2.0); 7.3430 (3.8); 7 .3395 (2.9); 7.2601 (41.0); 6.5015 (11.1); 6.4188 (2.3); 4.3343 (2.2); 4.3164 (7. 2); 4.2986 (7.4); 4.2808 (2.4); 2.2280 (1.0); 2.2198 (1.0); 2.2137 (0.6); 2. 2080 (1.8); 2.1992 (0.8); 2.1959 (1.2); 2.1876 (1.2); 2.1758 (0.8); 1.5523 (1.8 ); 1.3639 (7.6); 1.3460 (16.0); 1.3282 (7.7); 1.3040 (0.6); 1.2962 (0.6); 1.2823 (1.4); 1.2783 (1.3); 1.2688 (4.2); 1.2633 (5.0); 1.2621 (5.1); 1.2570 (3.8) ;1.2542(3.4);1.2500(3.6);1.2422(1.8);1.2298(0.8);1.2220(1.0);1.2164( 1.7); 1.2082 (3.5); 1.2013 (2.6); 1.1961 (2.2); 1.1880 (3.8); 1.1810 (2.4); 1.1740 (0.8); 1.1676 (0.8); 1.1364 (0.6); 1.1162 (0.6); 0.8986 (1.2); 0.8817 (3 .9); 0.8640 (1.6); 0.0080 (0.7); -0.0002 (23.2); -0.0084 (1.0)
II-086: ^1H -NMR (400.0 MHz, CDCl3):
δ=15.6668 (1.3); 8.3371 (5.0); 7.3400 (1.5); 7.3346 (0.8); 7.3268 (1.7); 7.3236 (1.0); 7.3214 (1.0); 7.3180 (2.2); 7.3105 (0.9); 7.3049 (2.1); 7.2629 (9.4) ;7.2111(2.2);7.2057(0.7);7.1942(0.8);7.1896(3.4);7.1844(0.8);7.1731( 0.6); 7.1678 (1.5); 6.4157 (5.6); 5.2986 (0.6); 3.8543 (16.0); 2.2279 (0.5); 2.2199 (0.6); 2.2117 (0.6); 2.2080 (0.9); 2.1957 (0.6); 2.1878 (0.6); 1.2683 (1 .3); 1.2613 (1.7); 1.2548 (1.9); 1.2496 (1.6); 1.2420 (0.9); 1.2386 (0.6); 1 .2277 (1.3); 1.2208 (1.5); 1.2138 (1.2); 1.2082 (1.0); 1.2003 (1.7); 1.1936 (1. 1);-0.0002 (5.4)
II-097: ^1H -NMR (400.0 MHz, _d6 -DMSO):
δ = 14.7341 (0.5); 8.5214 (16.0); 8.3976 (0.9); 7.6824 (4.2); 7.6782 (5.2); 7.6628 (4.4); 7.6594 (5.9); 7.5689 (1.8); 7.5639 (2.3); 7.5505 (5.0); 7.5454 (5.3) ;7.5324(6.6);7.5264(5.2);7.5146(5.9);7.5107(5.7);7.4963(2.9);7.4924( 2.3); 7.4863 (0.6); 7.4687 (6.6); 7.4641 (4.5); 7.4508 (4.2); 7.4453 (3.1); 5.8902 (13.4); 2.6769 (0.7); 2.6721 (1.0); 2.6675 (0.7); 2.5256 (2.8); 2.5210 (3 .6);2.5121 (58.0);2.5076 (128.8);2.5030 (180.6);2.4985 (127.5);2.4939 (57.4);2 .4635 (0.6); 2.3629 (0.7); 2.3512 (1.6); 2.3401 (1.9); 2.3307 (4.0); 2.3250 (1. 8); 2.3198 (2.2); 2.3112 (1.7); 2.2993 (0.8); 2.2171 (3.0); 1.2373 (1.4); 1. 2265 (3.7); 1.2188 (6.1); 1.2111 (3.9); 1.2063 (3.6); 1.1987 (5.4); 1.1911 (2.5 ); 1.1811 (0.6); 1.1747 (0.6); 1.1688 (0.6); 1.1550 (0.7); 1.1440 (2.5); 1.1366 (5.6); 1.1252 (6.9); 1.1179 (4.6); 1.1073 (1.4); 1.0896 (0.6); 1.0694 (0.6) ;1.0631(0.6);0.0080(2.7);-0.0002(99.6);-0.0085(3.0)
II-098: ^1H -NMR (400.0 MHz, CDCl3):
δ = 15.4957 (1.0); 8.3379 (5.0); 7.5483 (0.9); 7.5441 (1.3); 7.5306 (1.0); 7.5286 (1.1); 7.5254 (1.3); 7.4320 (0.6); 7.4182 (1.3); 7.4133 (1.3); 7.3999 (2.1) ;7.3950(1.6);7.3816(1.5);7.3777(1.3);7.3630(0.6);7.2608(14.2);7.2543( 1.2); 7.2523 (1.0); 7.2406 (1.3); 7.2356 (0.9); 6.0982 (5.8); 3.8347 (16.0); 2.2465 (0.5); 2.2347 (0.9); 2.2224 (0.5); 2.2143 (0.6); 1.5480 (2.3); 1.3021 (0 .5); 1.2898 (1.1); 1.2831 (1.6); 1.2755 (1.5); 1.2712 (1.9); 1.2632 (1.4); 1 .2546 (0.6); 1.2409 (0.8); 1.2383 (0.6); 1.2326 (1.4); 1.2257 (1.0); 1.2207 (0. 7); 1.2186 (0.6); 1.2124 (1.5); 1.2052 (1.0); 0.8817 (1.2); 0.0079 (0.5); -0 .0002 (16.7); -0.0085 (0.6)
II-481: ^1H -NMR (400.0 MHz, CDCl3):
δ = 8.3063 (1.3); 8.1229 (13.2); 7.5191 (1.6); 7.3127 (3.7); 7.3064 (3.7); 7.2918 (3.6); 7.2855 (3.8); 7.2602 (301.6); 7.2547 (4.9); 7.2397 (3.3); 7.2331 (4.3) ;7.2184(3.9);7.1415(2.9);7.1351(2.7);7.1219(3.2);7.1154(2.8);7.1005( 1.9); 7.0941 (1.7); 6.9962 (1.7); 6.0523 (1.6); 5.9673 (16.0); 3.8456 (4.2); 2.1588 (0.6); 2.1473 (1.4); 2.1392 (1.4); 2.1276 (2.5); 2.1156 (1.4); 2.1072 (1 .8); 2.1038 (5.8); 2.0559 (0.7); 2.0453 (1.0); 1.5437 (2.5); 1.4323 (1.6); 1 .4029 (1.4); 1.3956 (2.8); 1.3851 (3.8); 1.3737 (2.9); 1.3438 (1.6); 1.3315 (4. 8); 1.3240 (3.4); 1.3119 (4.0); 1.3048 (2.8); 1.2597 (0.8); 1.2420 (0.8); 0. 1461 (0.9); 0.0080 (8.4); -0.0002 (293.8); -0.0085 (8.4); -0.1500 (0.9)
II-542: ^1H -NMR (400.0 MHz, CDCl3):
δ = 15.4340 (0.8); 8.2827 (5.1); 7.4795 (2.4); 7.4770 (2.7); 7.4586 (4.0); 7.4575 (4.3); 7.3844 (2.2); 7.3663 (1.6); 7.3622 (1.3); 7.3441 (1.1); 7.2629 (27.2) 5.9425 (6.1); 5.3021 (3.4); 3.8404 (16.0); 2.2491 (0.8); 2.2289 (0.5); 1.3107 ( 1.0); 1.3036 (1.3); 1.2987 (1.0); 1.2958 (1.0); 1.2916 (1.4); 1.2839 (0.7); 1.2641 (0.5); 1.2590 (0.9); 1.2509 (1.6); 1.2441 (0.9); 1.2390 (0.8); 1.2307 (1 .4); 1.2237 (1.0); -0.0002 (16.0)
IV-137: ^1H -NMR (400.6 MHz, CDCl3):
δ = 8.7372 (1.3); 8.2124 (6.9); 7.5189 (1.0); 7.5146 (1.1); 7.4992 (1.0); 7.4958 (1.4); 7.3883 (1.0); 7.3834 (1.1); 7.3705 (1.6); 7.3656 (1.4); 7.3526 (1.3) ;7.3488(1.2);7.3340(0.5);7.2625(20.7);7.2497(1.4);7.2452(1.1);7.2318( 1.2); 7.2266 (1.0); 6.1133 (6.3); 3.1625 (1.4); 3.1512 (16.0); 2.1897 (0.6); 2.1815 (0.6); 2.1700 (1.1); 2.1578 (0.7); 2.1496 (0.7); 1.4609 (2.4); 1.4413 (8 .0); 1.3228 (0.6); 1.3024 (1.7); 1.2982 (1.6); 1.2915 (1.4); 1.2869 (1.4); 1 .2771 (1.0); 1.2641 (2.2); 1.2604 (2.2); 1.2504 (2.1); 1.2435 (1.3); 1.2302 (1. 8); 1.2233 (1.1); 1.2159 (0.6); 0.8987 (1.0); 0.8818 (3.4); 0.8641 (1.4); -0 .0002 (12.6)
IV-138: ^1H -NMR (400.0 MHz, CDCl3):
δ = 8.9957 (2.7); 8.2165 (8.8); 7.5371 (1.4); 7.5331 (1.6); 7.5173 (1.7); 7.5139 (2.1); 7.4306 (0.7); 7.4259 (0.8); 7.4119 (1.8); 7.4071 (1.8); 7.3930 (1.7) ;7.3904(1.8);7.3875(2.0);7.3718(2.1);7.3681(2.0);7.3532(1.0);7.3495( 0.9); 7.2621 (60.7); 7.2570 (2.5); 7.2527 (1.7); 7.2387 (1.8); 7.2337 (1.6); 6.1027 (7.9); 5.2999 (3.4); 4.1308 (1.0); 4.1130 (1.0); 3.3356 (0.7); 3.3103 (0 .5);3.1614(15.9);2.1814(1.1);2.1736(1.2);2.1620(1.4);2.1497(0.9);2 .1415 (0.8); 2.1309 (0.7); 2.0824 (2.7); 2.0451 (4.9); 2.0320 (16.0); 1.3554 (0. 5); 1.3477 (0.8); 1.3408 (1.8); 1.3332 (4.4); 1.3210 (1.7); 1.2951 (1.2); 1. 2844 (5.8); 1.2773 (3.2); 1.2647 (2.9); 1.2593 (4.9); 1.2415 (1.8); 1.1986 (0.7 ); 1.1808 (1.3); 1.1629 (0.7); 1.1362 (0.7); 1.1184 (1.4); 1.1005 (0.7); 0.0079 (1.0); -0.0002 (35.8); -0.0085 (1.1)
IV-140: ^1H -NMR (400.0 MHz, CDCl3):
δ = 8.9607 (1.5); 8.2148 (5.1); 7.5353 (0.9); 7.5309 (1.2); 7.5176 (0.9); 7.5155 (1.0); 7.5121 (1.3); 7.4206 (0.6); 7.4068 (1.3); 7.4019 (1.3); 7.3890 (1.5) ;7.3846(1.2);7.3827(1.1);7.3713(1.4);7.3674(1.2);7.3527(0.6);7.2608( 15.4); 7.2576 (1.6); 7.2529 (1.0); 7.2509 (0.9); 7.2395 (1.2); 7.2341 (0.9); 6.0435 (5.7); 5.2998 (0.6); 3.2570 (16.0); 3.0206 (15.0); 2.1659 (0.8); 2.1454 (0 .5); 1.3328 (0.9); 1.3256 (1.0); 1.3204 (1.2); 1.3178 (1.1); 1.3139 (1.0); 1 .3062 (1.1); 1.2890 (0.8); 1.2843 (0.9); 1.2795 (1.5); 1.2728 (1.0); 1.2689 (0. 8); 1.2591 (1.7); 1.2526 (1.1); 0.0079 (0.5); -0.0002 (20.0); -0.0085 (0.6)

Compounds of the invention can be prepared by the methods specified in the scheme below.

Starting compounds of the 4-methyl-5-arylpyrimidine type are described by Kondo et al., Chem. Pharm. Bull. 37 (1989) 2814 for 2,4-dimethyl-5-phenylpyrimidine from 5-bromopyrimidine or 5-iodopyrimidine.

Starting compounds of 4-halo-5-arylpyrimidines (halogen=chlorine, bromine, iodine) can be prepared from suitable 4-hydroxy-5-arylpyrimidines by chlorination, for example with phosphorous oxychloride. Such a method is described, for example, in Shestakov et al., Tetrahedron 73 (2017) 3939 for the preparation of 4-chloro-5-(4-chlorophenyl)-2-phenylpyrimidine.

Initially, by known methods, for example, an amidine or a salt of an amidine is prepared with an enol ester or a 3-hydroxyacryloyl derivative, optionally with an inorganic base, in a suitable solvent at a reaction temperature between -30 and 180°C. Condensed with organic or organometallic bases, such as potassium carbonate, sodium ethoxide or hexamethyldisilazide (WO 2008156726, WO 2012171863):

Subsequently, the pyrimidine can be halogenated by known methods at the 5-position using a halogenating agent, such as N-iodo- or N-bromosuccinimide or bromine (J. Med. Chem. 51 (2008) 5766 ):
After that, cross-coupling reactions such as Suzuki coupling (International Publication No. 2014081617, International Publication No. 2007146824), Stille coupling (J. Org. Chem. 74 (2009) 5599), Kumada coupling (J. Org. Chem. 73 (2008) 162) or Negishi coupling (Synthesis 48 (2016) 504).

Subsequently, pyrimidone can be converted to 4-halopyrimidine, for example by known halogenating agents such as phosphorus oxychloride or thionyl bromide. This is followed by Heck coupling under metal catalysis (Tetrahedron Lett. 28 (1987) 3039) to give alkenyloxyacrylates, which are then hydrolyzed to pyruvic acid (J. Org. Chem. 80 (2015) 2554).

It is also possible to use the corresponding triflates or diazonium salts instead of 4-halopyridines.

Possible alternative reaction regimes are shown in the two schemes below:

Instead of 2-methoxyacrylate, the corresponding 2-enaminoacrylate (Acta. Chem. Scand. 50 (1996) 316; Synthesis 1989, 414) was added in a suitable solvent within the temperature range of -78°C to 180°C. When used in , an enamino ester is obtained as an intermediate, which is then hydrolyzed to pyruvate (J. Org. Chem. 80 (2015) 2554).

A further alternative method proceeds from pyrimidine-4-carbaldehyde, which can be converted to alkenyloxyacrylates or enaminoacrylates via a Wittig-Horner reaction and hydrolyzed as described above (J. Org. Chem. 80 (2015) 2554).

Additionally, iron-catalyzed addition from the corresponding 4-alkylpyrimidine (Tetrahedron 70 (2014) 3056) followed by oxidation, e.g. by Dess-Martin reagent (J. Org. Chem. 81 (2016) 3890), or by acetic acid It is possible to prepare 2-keto acids or esters or amides using copper (J. Org. Chem. 79 (2014) 11735) or by Swern oxidation (WO 2013057468).

In addition, it is possible to deprotonate pyrimidine alkyl compounds with strong bases, such as lithium diisopropylamide, and react them with oxalate ester derivatives (Journal of Organic Chemistry 80 (2015) 2554, Bioorg. Med. Chem. 14 (2006) 8420).

In addition, it is possible to convert the compounds of the invention into the desired target compounds (I) by reacting with oxalate ester derivatives, for example with the following orthoesters (J.C. Medina et al., Tetrahedron Lett. .49 (2008) 1768; J. Scherkenbeck et al., J. Org. Chem. 80 (2015) 2554-2561):

The carboxamide derivatives, carbohydrazides, methylidene hydrazides and optionally substituted N-hydroxycarboxamides (I) of the invention are synthesized from the corresponding acids by reaction with coupling reagents, bases and the respective amine or hydrazine derivatives. be done.

For this purpose, a wide variety of different methods are available in the literature (Tetrahedron 61 (2005) 10827; WO 2006/105051, p. 8).

Alkylidene hydrazides can be prepared, for example, by heating a primary hydrazide with a suitable carbonyl compound (Arch. Pharm. Chem. Life Sci. 350 (2017) e1600256).

The collection of compounds of formula (I) and/or salts thereof that can be synthesized by the above reactions can also be prepared in a parallelized manner, in which case it can be carried out manually, partially or fully automated. This can be achieved in the following manner. For example, it is possible to automate the performance of reactions, work-up or purification of products and/or intermediates. Overall, this means that, for example, D. It is understood to mean the procedure described in Tiebes, Combinatorial Chemistry-Synthesis, Analysis, Screening (editor: Gunther Jung), Wiley, 1999, pages 1-34.

The compounds of formula (I) (and/or salts thereof) according to the invention, hereinafter collectively referred to as "compounds according to the invention", have demonstrated superior efficacy against a wide range of economically important monocotyledonous and dicotyledonous annual harmful plants. It has a weeding effect.

The invention therefore also provides a method for controlling unwanted plants or regulating plant growth, preferably in plant crops, comprising applying one or more compounds of the invention to plants (e.g. monocotyledonous or dicotyledonous). Noxious plants such as weeds or unwanted crop plants), seeds (e.g. grains, seeds or vegetative propagules, e.g. tubers or shoot parts with buds) or areas where plants grow (e.g. areas under cultivation) provide a method to do so. The compounds of the invention can be used, for example, before sowing (if appropriate by incorporation into the soil), pre-emergence or post-emergence. Without intending to limit the list to particular species, some representative examples of monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds of the present invention are as follows.

Genus of monocot harmful plants: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Platypus Genus Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Phleum (Poa), Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Genus of dicotyledonous weeds: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Pigweed Genus Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Thistle ( Cirsium), Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga), Gallium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Lindernia Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum , Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Senecio Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Taraxacum (Thlaspi), Trifolium, Urtica, Veronica, Viola, Xanthium.

Application of the compounds of the invention to the soil surface before germination completely prevents weed seedlings from budding, or the weeds grow until they reach the cotyledon stage, but then stop growing.

If the active compound is applied to the green parts of the plants after emergence, either growth stops after the treatment and the harmful plants remain in the growth stage at the time of application, or they die completely after a certain time and as a result are thus harmful to the crop plants. Competition by noxious weeds is eliminated extremely quickly and sustainably.

The compounds of the invention can be selective in crops of useful plants and can also be used as non-selective herbicides.

Because of their herbicidal and plant growth regulating properties, the active compounds can also be used to control harmful plants in crops of known or as yet undeveloped genetically modified plants. In general, transgenic plants have certain advantageous properties, such as resistance to certain active compounds used in the agricultural industry, in particular to certain herbicides, plant diseases or pathogens of plant diseases (such as certain insects or microorganisms (fungi, characterized by resistance to bacteria, viruses, etc.) Other specific characteristics relate to the harvested material, for example with respect to quality, quantity, shelf life, composition and specific ingredients. For example, transgenic plants with increased starch content or altered starch quality, or with a different fatty acid composition in the harvested material, are known. Further specific properties consist in tolerance or resistance to abiotic stress factors such as heat, cold, drought, salinity and UV radiation.

The compounds of formula (I) or salts thereof of the present invention are preferably used in economically important transgenic crops of useful and ornamental plants.

The compounds of formula (I) can be used as herbicides in crops of useful plants that are tolerant or made tolerant by genetic engineering to the phytotoxic effects of herbicides.

Conventional methods of creating new plants with modified properties compared to existing plants consist, for example, in traditional cultivation methods and in the generation of mutants. Alternatively, new plants with altered properties can be created using recombinant methods (see, for example, EP 0 221 044, EP 0 131 624). Described are, for example, genetic modification of crop plants for the purpose of modifying starch synthesized in the plant (e.g. WO 92/011376, WO 92/014827, WO 91/ 019806), the glufosinate type (see e.g. EP 0 242 236, EP 0 242 246) or the glyphosate type (WO 92/000377) or the sulfonylurea type (see eg EP 0 242 236, EP 0 242 246) or the sulphonylurea Transgenic crop plants resistant to certain herbicides or combinations or mixtures of these herbicides (European Patent Application Publication No. 0257993, US Patent No. 5,013,659), such as the trade name or designation Optimum(TM) GAT (Trademark) (glyphosate ALS resistant) transgenic crop plants, such as corn or soybean,
- transgenic crop plants capable of producing a Bacillus thuringiensis toxin (Bt toxin) that makes the plant resistant to certain pests, such as cotton (European Patent Application No. 0142924, European Patent Publication No. 0193259),
- transgenic crop plants with modified fatty acid composition (WO 91/013972),
- genetically modified crop plants with novel constituents or secondary metabolites that increase disease resistance, such as novel phytoalexins (EP 0 309 862, EP 0 464 461);
- genetically modified plants with reduced photorespiration with higher yield and higher stress tolerance (European Patent Application No. 0305398);
- transgenic crop plants that produce pharmaceutically or diagnostically important proteins (“molecular farming”);
- transgenic crop plants characterized by higher yield or better quality,
- transgenic crop plants identified, for example, by a combination of the above-mentioned novel characteristics (“gene stacking”)
Here are some examples.

A large number of molecular biological techniques that can be used to generate new transgenic plants with altered properties are known in principle; for example, I. Potrykus and G. Spangenberg (ed.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg or Christou, Trends in Plant Science 1 (1996) 423-431).

For such genetic manipulation, nucleic acid molecules can be introduced into the plasmid that allow recombinant mutagenesis or sequence changes of the DNA sequence. Standard methods can be used, for example, to make base exchanges, to remove parts of the sequence, or to add natural or synthetic sequences. To join DNA fragments together, adapters or linkers can be placed on the fragments. For example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene und Klone" [Genes and Clones], VCH Weinheim 2nd edition 1996. Please refer.

For example, the creation of plant cells with reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, sense RNA, or transcript of the above-mentioned gene product to achieve a co-suppression effect. This can be achieved by expressing at least one appropriately constructed ribozyme that specifically cleaves. To achieve this goal, we first need to prepare DNA molecules that include the entire coding sequence of the gene product, including any flanking sequences that may be present, and DNA molecules that only include portions of the coding sequence (in this case, these portions). (but need to be long enough to have an antisense effect in cells) can also be used. It is also possible to use DNA sequences that have a high degree of homology to, but are not completely identical to, the coding sequences of the gene products.

When expressing nucleic acids in plants, the synthesized protein can be localized to any desired compartment of the plant cell. However, in order to achieve localization to a specific compartment, it is possible, for example, to link a coding region that ensures localization to a specific compartment to the DNA sequence. Such sequences are known to those skilled in the art (eg, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850). ; see Sonnewald et al., Plant J. 1 (1991), 95-106). Nucleic acid molecules can also be expressed in organelles of plant cells.

Transgenic plant cells can be regenerated by known techniques to produce whole plants. In principle, the transgenic plants may be plants of any desired plant species, ie monocots as well as dicots. It is thus possible to obtain transgenic plants whose properties are altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or by expression of heterologous (=foreign) genes or gene sequences.

growth regulators such as 2,4-D, dicamba, or essential plant enzymes such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD). resistant to inhibiting herbicides or to herbicides of the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazole and similar active compounds, or to any desired combination of these active compounds Compound (I) of the present invention can be preferably used in transgenic crops.

The compounds of the invention can be particularly preferably used in transgenic crop plants that are tolerant to combinations of glyphosate and glufosinate, glyphosate and sulfonylureas or imidazolinones. Most preferably, the compounds of the invention can be used in transgenic crop plants, such as corn or soybean, for example under the trade name Optimum™ GAT™ (glyphosate ALS resistant).

When the active compounds of the invention are used in transgenic crops, not only the effects against harmful plants observed in other crops occur, but also effects that are specific to application to a particular transgenic crop, e.g. an altered or specifically expanded range of weeds obtained, variations in the application rates that can be used for application, preferably superior combinations with herbicides to which the transgenic crop is tolerant, and growth and yield of the transgenic crop plants. There will also be an impact on

The invention therefore also relates to the use of the compounds of the invention of formula (I) as herbicides for controlling harmful plants in transgenic crop plants.

The compounds of the invention can be applied in the customary formulations in the form of wettable powders, emulsions, spray solutions, dust products or granules. Therefore, the invention also provides herbicidal plant growth regulating compositions comprising the compounds of the invention.

The compounds of the invention can be formulated in various ways according to the required biological and/or physicochemical parameters. Possible formulations include, for example: wettable powders (WP), aqueous solutions (SP), aqueous solutions, emulsions (EC), emulsion formulations (EW), e.g. oil-in-water and water-in-oil emulsion formulations, sprays. Liquids, suspensions (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), powder products (DP), dressings, granules for scattering and soil application. , granules (GR) in the form of microgranules, spray granules, absorbents and adsorption granules, wettable granules (WG), aqueous granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in Winnacker-Kuchler, "Chemische Technologie" [Chemical Technology], Vol. 7, C. Hanser Verlag Munich, 4th edition, 1986, Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N. Y. , 1973, K. Martens, "Spray Drying" Handbook, 3rd edition, 1979, G. Goodwin Ltd. Listed in London.

The required formulation auxiliaries (such as inert materials, surfactants, solvents and further additives) are known as well, for example Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd edition, Darland. Books, Caldwell N. J. ;H. v. Olphen, "Introduction to Clay Colloid Chemistry", 2nd edition, J. Wiley & Sons, N. Y. ;C. Marsden, "Solvents Guide", 2nd edition, Interscience, N. Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp. , Ridgewood N. J. ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc. , N. Y. 1964; Schonfeldt, “Grenzflachenaktive Athylenoxidaddukte” [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesell. , Stuttgart 1976; Winnacker-Kuchler, "Chemische Technologie", Vol. 7, C. Described in Hanser Verlag Munich, 4th edition 1986.

Based on these formulations, combinations with other active compounds, such as insecticides, acaricides, herbicides, fungicides, as well as safeners, fertilizers and/or growth regulators, can be added, for example to the final formulation. It is also possible to produce it in form or as a tank mix.

Active compounds which can be used in combination with compounds of the invention in mixed formulations or tank mixes are described, for example, in Weed Research 26 (1986) 441-445 or in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and the literature cited therein, such as acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenyl Known active compounds based on the inhibition of pyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase. Known herbicides or plant growth regulators that can be combined with the compounds of the invention are, for example, the active compounds designated by their "common name" or chemical name or code number according to the International Organization for Standardization (ISO). be done. Even if explicitly mentioned, they always include all usage forms, such as acids, salts, esters, and all isomeric forms, such as stereoisomers and optical isomers.

Examples of such herbicide mixing partners are:
Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, arachlor, alidochlor, alloxydim, alloxydim-sodium, ametrine, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2 -fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulfamate, anilophos, aslam, Atrazine, azafenidine, azimsulfuron, beflubutamide, benazoline, benazoline-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobiciclone, benzofenap, bicyclopyrone, bifenox, vilanafos, vilanafos-sodium, Bispyribac, Bispyribac-sodium, bromacil, bromobutide, bromophenoxime, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxynone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butyrate, caffetenstrol, carbetamide , carfentrazone, carfentrazone-ethyl, chloramben, chlorbromulon, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazone, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron , chlortal-dimethyl, chlorsulfuron, cinidone, cinidon-ethyl, synmethyline, sinosulfuron, clacyfos, cletodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, chloransulam, chloransulam-methyl, cumyluron, cyanamide, cyanazine, Cycloate, cyclopyranyl, cyclopyrimoleate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamine, -ethyl , 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, -isooctyl, -potassium and - Sodium, Daimeron (Daimron), Darapon, Dazomet, n-decanol, desmedifam, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2- Oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop -P-methyl, diclosulam, difenzocort, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefron, dimepiperate, dimethachlor, dimethamethrin, dimethenamide, dimethenamide-P, dimetrasulfuron, dinitramine, dinoterb, diphenamide, diquat, diquat Dibromide, dithiopyr, diuron, DNOC, Endothal, EPTC, esprocarb, etalfluralin, etametsulfuron, etametsulfuron-methyl, ethiodine, ethofumesate, ethoxifen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanide, F-9600, F- 5231, namely N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4 (1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrone, fentrazamide, flamprop, flamprop-M- Isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpir, flufenpir -ethyl, flumetulam, flumicrolac, flumicrolac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron , flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurutamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate -P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimethium, H-9201, i.e. O -(2,4-dimethyl-6-nitrophenyl)O-ethylisopropylphosphoramide thioate, halooxifene, halooxifene-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop -Ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, imazametabenz, imazametabenz-methyl , imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyl-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanophane, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, Ioxinil, ioxinyl-octanoate, -potassium and -sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, carbutyrate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl -3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacyl, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium and -butyl, mecoprop-P, Mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, metabenzthiazuron, metam, metamifop, metamitrone, metazachlor, metazosulfuron, metabenzothiaz Ron, methiopyrsulfuron, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metsulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, i.e. N- [3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5- Benzyloxypyrazole, nebulon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazone, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazone, oxasulfuron, oxadiclomefon, oxyfluorfen, paraquat, paraquat dichloride , pebrate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, petoxamide, petroleum, phenmedipham, picloram, picolinafen, pinoxafene, piperofos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, propoxydim, prometone, promethrin, Propachlor, propanil, propaquizafop, propazine, propam, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, piaflufen-ethyl, pyrasulfotol, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxifene, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxime, pyributicarb, pyridafol, pyridate, pyriftalide, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, Pyrithiobac-sodium, piroxasulfone, piroxsulam, quinclorac, quinmerac, quinocramine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, setoxydim, siduron, simazine , cymetrin, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249, i.e., 1-ethoxy-3-methyl-1-oxobut-3-ene- 2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn- 1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebutiuron, tefuryltrione, tenbotrione, tepraloxydim, terbacil, telbucarb, terbumetone, terbutylazine, terbutryn, tenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron- Methyl, thiobencarb, thiafenacil, tolpirate, topramezone, tralkoxydim, triafamone, trialate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietadine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazine, Trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidine) -2-yl)oxy]benzyl}aniline, and the following compounds:

Examples of plant growth regulators as possible mixing partners are:
Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid , daminozide, dazomet, n-decanol, dikeglac, dikeglac-sodium, endotal, endotal-dipotassium, -disodium and mono(N,N-dimethylalkylammonium), ethephon, flumetraline, flurenol, flurenol-butyl, flurprimi Dole, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester, maleic hydrazide, mepiquat Chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthyl acetic acid, 2-naphthyloxyacetic acid, nitronitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, Paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, technazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, Titodef, Uniconazole, Uniconazole-P.

Phytotoxicity which can be used in combination with the compounds of formula (I) according to the invention and optionally in combination with further active compounds such as insecticides, acaricides, herbicides, fungicides, etc. as listed above. The agent is preferably selected from the group consisting of:

ここで、記号および指数は以下の通りに定義される：
n_Aは0～5、好ましくは0～3の自然数を表し；
R_A ¹はハロゲン、（C₁～C₄）－アルキル、（C₁～C₄）－アルコキシ、ニトロまたは（C₁～C₄）－ハロアルキルを表し；
W_AはNおよびO基の1～3個の環ヘテロ原子を有する部分不飽和または芳香族5員複素環の群の非置換または置換二価複素環式基を表し、少なくとも1個の窒素原子および最大1個の酸素原子が環中に存在し、好ましくは（W_A ¹）～（W_A ⁴）の群の基

を表し、
m_Aは0または1を表し；
R_A ²はOR_A ³、SR_A ³またはNR_A ³R_A ⁴、または少なくとも1個の窒素原子と最大3個の好ましくはOおよびSからなる群のヘテロ原子とを有する飽和もしくは不飽和の3～7員複素環を表し、窒素原子を介して（S1）中のカルボニル基に結合しており、非置換であるか、または（C₁～C₄）－アルキル、（C₁～C₄）－アルコキシもしくは場合により置換されたフェニルからなる群の基によって置換されており、好ましくは式OR_A ³、NHR_A ⁴またはN（CH₃）₂、特に式OR_A ³の基であり；
R_A ³は水素、または好ましくは合計1～18個の炭素原子を有する非置換もしくは置換脂肪族炭化水素基であり；
R_A ⁴は水素、（C₁～C₆）－アルキル、（C₁～C₆）－アルコキシまたは置換もしくは非置換フェニルであり；
R_A ⁵はH、（C₁～C₈）－アルキル、（C₁～C₈）－ハロアルキル、（C₁～C₄）－アルコキシ－（C₁～C₈）－アルキル、シアノまたはCOOR_A ⁹であり、R_A ⁹は水素、（C₁～C₈）－アルキル、（C₁～C₈）－ハロアルキル、（C₁～C₄）－アルコキシ－（C₁～C₄）－アルキル、（C₁～C₆）－ヒドロキシアルキル、（C₃～C₁₂）－シクロアルキルまたはトリ－（C₁～C₄）－アルキルシリルを表し；
R_A ⁶、R_A ⁷、R_A ⁸は同一であるかまたは異なり、水素、（C₁～C₈）－アルキル、（C₁～C₈）－ハロアルキル、（C₃～C₁₂）－シクロアルキルまたは置換もしくは非置換フェニルである；
好ましくは：
a）ジクロロフェニルピラゾリン－3－カルボン酸型の化合物（S1^a）、好ましくは1－（2，4－ジクロロフェニル）－5－（エトキシカルボニル）－5－メチル－2－ピラゾリン－3－カルボン酸、エチル1－（2，4－ジクロロフェニル）－5－（エトキシカルボニル）－5－メチル－2－ピラゾリン－3－カルボキシレート（S1－1）（「メフェンピル－ジエチル」）、および国際公開第91／07874号に記載される関連化合物などの化合物；
b）ジクロロフェニルピラゾールカルボン酸の誘導体（S1^b）、好ましくはエチル1－（2，4－ジクロロフェニル）－5－メチルピラゾール－3－カルボキシレート（S1－2）、エチル1－（2，4－ジクロロフェニル）－5－イソプロピルピラゾール－3－カルボキシレート（S1－3）、エチル1－（2，4－ジクロロフェニル）－5－（1，1－ジメチルエチル）ピラゾール－3－カルボキシレート（S1－4）ならびに欧州特許第333131号および欧州特許第269806号に記載される関連化合物などの化合物；
c）1，5－ジフェニルピラゾール－3－カルボン酸の誘導体（S1^c）、好ましくはエチル1－（2，4－ジクロロフェニル）－5－フェニルピラゾール－3－カルボキシレート（S1－5）、メチル1－（2－クロロフェニル）－5－フェニルピラゾール－3－カルボキシレート（S1－6）および欧州特許第268554号に記載される関連化合物などの化合物、例えば；
d）トリアゾールカルボン酸型の化合物（S1^d）、好ましくはフェンクロラゾール（－エチルエステル）、すなわちエチル1－（2，4－ジクロロフェニル）－5－トリクロロメチル－（1H）－1，2，4－トリアゾール－3－カルボキシレート（S1－7）、ならびに欧州特許第174562号および欧州特許第346620号に記載される関連化合物などの化合物；
e）5－ベンジル－もしくは5－フェニル－2－イソオキサゾリン－3－カルボン酸または5，5－ジフェニル－2－イソオキサゾリン－3－カルボン酸型の化合物（S1^e）、好ましくはエチル5－（2，4－ジクロロベンジル）－2－イソオキサゾリン－3－カルボキシレート（S1－8）または5－フェニル－2－イソオキサゾリン－3－カルボキシレート（S1－9）および国際公開第91／08202号に記載される関連化合物、または特許出願、国際公開第95／07897号に記載される5，5－ジフェニル－2－イソオキサゾリン－3－カルボン酸（S1－10）またはエチル5，5－ジフェニル－2－イソオキサゾリン－3－カルボキシレート（S1－11）（「イソキサジフェン－エチル」）または、n－プロピル5，5－ジフェニル－2－イソオキサゾリン－3－カルボキシレート（S1－12）またはエチル5－（4－フルオロフェニル）－5－フェニル－2－イソオキサゾリン－3－カルボキシレート（S1－13）などの化合物。 S1) Compound of formula (S1)

Here, symbols and exponents are defined as follows:
n _A represents a natural number from 0 to 5, preferably from 0 to 3;
R _A ¹ represents halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, nitro or (C ₁ -C ₄ )-haloalkyl;
W _A represents an unsubstituted or substituted divalent heterocyclic group of the group of partially unsaturated or aromatic 5-membered heterocycles with 1 to 3 ring heteroatoms of N and O groups, at least one nitrogen atom and at most one oxygen atom is present in the ring, preferably groups of the group (W _A ¹ ) to (W _A ⁴ )

represents,
m _A represents 0 or 1;
R _A ² is OR _A ³ , SR _A ³ or NR _A ³ R _A ⁴ , or a saturated or unsaturated compound having at least one nitrogen atom and up to 3 heteroatoms, preferably of the group consisting of O and S. It represents a 3- to 7-membered heterocycle, is bonded to the carbonyl group in (S1) via the nitrogen atom, and is unsubstituted or (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy or optionally substituted phenyl, preferably a group of the formula OR _A ³ , NHR _A ⁴ or N(CH ₃ ) ₂ , especially a group of the formula OR _A ³ ;
R _A ³ is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group, preferably having a total of 1 to 18 carbon atoms;
R _A ⁴ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkoxy or substituted or unsubstituted phenyl;
R _A ⁵ is H, (C ₁ -C ₈ )-alkyl, (C ₁ -C ₈ )-haloalkyl, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₈ )-alkyl, cyano or COOR _A ⁹ , and R _A ⁹ is hydrogen, (C ₁ -C ₈ )-alkyl, (C ₁ -C ₈ )-haloalkyl, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl, (C ₁ -C ₆ )-hydroxyalkyl, (C ₃ -C ₁₂ )-cycloalkyl or tri-(C ₁ -C ₄ )-alkylsilyl;
R _A ⁶ , R _A ⁷ , R _A ⁸ are the same or different and are hydrogen, (C ₁ -C ₈ )-alkyl, (C ₁ -C ₈ )-haloalkyl, (C ₃ -C ₁₂ )-cyclo is alkyl or substituted or unsubstituted phenyl;
Preferably:
a) compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (S1 ^a ), preferably 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, Ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) (“mefenpyr-diethyl”), and WO 91/07874 Compounds such as related compounds described in No.
b) Derivatives of dichlorophenylpyrazole carboxylic acids (S1 ^b ), preferably ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl) )-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4), and Compounds such as related compounds described in EP 333131 and EP 269806;
c) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 ^c ), preferably ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1 Compounds such as -(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related compounds described in EP 268554, for example;
d) Compounds of the triazole carboxylic acid type (S1 ^d ), preferably fenchlorazole (-ethyl ester), i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4 - compounds such as triazole-3-carboxylate (S1-7) and related compounds described in EP 174 562 and EP 346 620;
e) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (S1 ^e ), preferably ethyl 5-( 2,4-Dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and WO 91/08202 Related compounds described or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1-10) or ethyl 5,5-diphenyl-2 as described in patent application WO 95/07897 -Isoxazoline-3-carboxylate (S1-11) ("isoxadifen-ethyl") or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-( Compounds such as 4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13).

R_B ¹はハロゲン、（C₁～C₄）－アルキル、（C₁～C₄）－アルコキシ、ニトロまたは（C₁～C₄）－ハロアルキルを表し；
n_Bは0～5、好ましくは0～3の自然数を表し；
R_B ²はOR_B ³、SR_B ³、NR_B ³R_B ⁴、または少なくとも1個の窒素原子と最大3個の好ましくはOおよびSの群のヘテロ原子とを有する飽和もしくは不飽和の3～7員複素環を表し、窒素原子を介して（S2）中のカルボニル基に結合しており、非置換である、または（C₁～C₄）－アルキル、（C₁～C₄）－アルコキシもしくは場合により置換されたフェニルの群の基によって置換されており、好ましくは式OR_B ³、NHR_B ⁴またはN（CH₃）₂、特に式OR_B ³の基であり；
R_B ³は水素または好ましくは合計1～18個の炭素原子を有する非置換もしくは置換脂肪族炭化水素基を表し；
R_B ⁴は水素、（C₁～C₆）－アルキル、（C₁～C₆）－アルコキシまたは置換もしくは非置換フェニルを表し；
T_Bは非置換である、または1個もしくは2個の（C₁～C₄）－アルキル基によって、または［（C₁～C₃）－アルコキシ］カルボニルによって置換された（C₁またはC₂）－アルカンジイル鎖を表す）；
好ましくは：
a）8－キノリンオキシ酢酸型の化合物（S2^a）、好ましくは
1－メチルヘキシル（5－クロロ－8－キノリンオキシ）アセテート（「クロキントセット－メキシル」）（S2－1）、
（1，3－ジメチルブタ－1－イル）（5－クロロ－8－キノリンオキシ）アセテート（S2－2）、
4－アリルオキシブチル（5－クロロ－8－キノリンオキシ）アセテート（S2－3）、
1－アリルオキシプロパ－2－イル（5－クロロ－8－キノリンオキシ）アセテート（S2－4）、
エチル（5－クロロ－8－キノリンオキシ）アセテート（S2－5）、
メチル（5－クロロ－8－キノリンオキシ）アセテート（S2－6）、
アリル（5－クロロ－8－キノリンオキシ）アセテート（S2－7）、
2－（2－プロピリデンイミノキシ）－1－エチル（5－クロロ－8－キノリンオキシ）アセテート（S2－8）、2－オキソプロパ－1－イル（5－クロロ－8－キノリンオキシ）アセテート（S2－9）ならびに欧州特許出願公開第86750号、欧州特許出願公開第94349号および欧州特許出願公開第191736号または欧州特許出願公開第0492366号に記載される関連化合物、ならびに（5－クロロ－8－キノリンオキシ）酢酸（S2－10）、その水和物および塩、例えば国際公開第2002／34048号に記載されるそのリチウム、ナトリウム、カリウム、カルシウム、マグネシウム、アルミニウム、鉄、アンモニウム、四級アンモニウム、スルホニウムまたはホスホニウム塩；
b）（5－クロロ－8－キノリンオキシ）マロン酸型の化合物（S2^b）、好ましくはジエチル（5－クロロ－8－キノリンオキシ）マロネート、ジアリル（5－クロロ－8－キノリンオキシ）マロネート、メチルエチル（5－クロロ－8－キノリンオキシ）マロネートおよび欧州特許出願公開第0582198号に記載される関連化合物などの化合物。 S2) Quinoline derivatives of formula (S2) where symbols and indices are defined as follows:

R _B ¹ represents halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, nitro or (C ₁ -C ₄ )-haloalkyl;
n _B represents a natural number from 0 to 5, preferably from 0 to 3;
R _B ² is OR _B ³ , SR _B ³ , NR _B ³ R _B ⁴ , or a saturated or unsaturated 3 with at least one nitrogen atom and up to 3 heteroatoms, preferably of the group O and S. ~ represents a 7-membered heterocycle, is bonded to the carbonyl group in (S2) via the nitrogen atom, and is unsubstituted, or (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )- substituted by a radical of the group alkoxy or optionally substituted phenyl, preferably a radical of the formula OR _B ³ , NHR _B ⁴ or N(CH ₃ ) ₂ , especially a radical of the formula OR _B ³ ;
R _B ³ represents hydrogen or an unsubstituted or substituted aliphatic hydrocarbon group, preferably having a total of 1 to 18 carbon atoms;
R _B ⁴ represents hydrogen, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkoxy or substituted or unsubstituted phenyl;
T _B is unsubstituted or substituted by one or two (C ₁ -C ₄ )-alkyl groups or by [(C ₁ -C ₃ )-alkoxy]carbonyl (C ₁ or C ₂ )-represents an alkanediyl chain);
Preferably:
a) Compounds of the 8-quinolineoxyacetic acid type (S2 ^a ), preferably
1-Methylhexyl (5-chloro-8-quinolineoxy) acetate (“Cloquintocet-mexyl”) (S2-1),
(1,3-dimethylbut-1-yl)(5-chloro-8-quinolineoxy)acetate (S2-2),
4-allyloxybutyl (5-chloro-8-quinolineoxy) acetate (S2-3),
1-allyloxyprop-2-yl (5-chloro-8-quinolineoxy) acetate (S2-4),
Ethyl (5-chloro-8-quinolineoxy)acetate (S2-5),
Methyl (5-chloro-8-quinolineoxy)acetate (S2-6),
Allyl (5-chloro-8-quinolineoxy)acetate (S2-7),
2-(2-propylideniminoxy)-1-ethyl (5-chloro-8-quinolineoxy) acetate (S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolineoxy) acetate ( S2-9) and related compounds described in EP 86750, EP 94349 and EP 191736 or EP 0 492 366, and (5-chloro-8 - quinolineoxy)acetic acid (S2-10), its hydrates and salts, such as its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium as described in WO 2002/34048 , sulfonium or phosphonium salts;
b) Compounds of the (5-chloro-8-quinolineoxy)malonic acid type (S2 ^b ), preferably diethyl(5-chloro-8-quinolineoxy)malonate, diallyl(5-chloro-8-quinolineoxy)malonate, Compounds such as methyl ethyl (5-chloro-8-quinolineoxy) malonate and related compounds described in European Patent Application No. 0582198.

ここで、記号および指数は以下の通り定義される：
R_C ¹は（C₁～C₄）－アルキル、（C₁～C₄）－ハロアルキル、（C₂～C₄）－アルケニル、（C₂～C₄）－ハロアルケニル、（C₃～C₇）－シクロアルキル、好ましくはジクロロメチルを表し；
R_C ²、R_C ³は同一であるまたは異なり、水素、（C₁～C₄）－アルキル、（C₂～C₄）－アルケニル、（C₂～C₄）－アルキニル、（C₁～C₄）－ハロアルキル、（C₂～C₄）－ハロアルケニル、（C₁～C₄）－アルキルカルバモイル－（C₁～C₄）－アルキル、（C₂～C₄）－アルケニルカルバモイル－（C₁～C₄）－アルキル、（C₁～C₄）－アルコキシ－（C₁～C₄）－アルキル、ジオキソラニル－（C₁～C₄）－アルキル、チアゾリル、フリル、フリルアルキル、チエニル、ピペリジル、置換もしくは非置換フェニルを表す、あるいはR_C ²とR_C ³が一緒になって、置換または非置換複素環、好ましくはオキサゾリジン、チアゾリジン、ピペリジン、モルホリン、ヘキサヒドロピリミジンまたはベンゾオキサジン環を形成する；
好ましくは：
出芽前薬害軽減剤（土壌作用薬害軽減剤）として頻繁に使用されるジクロロアセトアミド型の活性化合物、例えば
「ジクロルミド」（N，N－ジアリル－2，2－ジクロロアセトアミド）（S3－1）、
Stauffer製の「R－29148」（3－ジクロロアセチル－2，2，5－トリメチル－1，3－オキサゾリジン）（S3－2）、
Stauffer製の「R－28725」（3－ジクロロアセチル－2，2－ジメチル－1，3－オキサゾリジン）（S3－3）、
「ベノキサコール」（4－ジクロロアセチル－3，4－ジヒドロ－3－メチル－2H－1，4－ベンゾオキサジン）（S3－4）、
PPG Industries製の「PPG－1292」（N－アリル－N－［（1，3－ジオキソラン－2－イル）メチル］ジクロロアセトアミド）（S3－5）、
Sagro－Chem製の「DKA－24」（N－アリル－N－［（アリルアミノカルボニル）メチル］ジクロロアセトアミド）（S3－6）、
NitrokemiaまたはMonsanto製の「AD－67」または「MON 4660」（3－ジクロロアセチル－1－オキサ－3－アザスピロ［4．5］デカン）（S3－7）、
TRI－Chemical RT製の「TI－35」（1－ジクロロアセチルアゼパン）（S3－8）、
「ジクロノン」（ジシクロノン）または「BAS145138」または「LAB145138」（S3－9）
BASF製の（（RS）－1－ジクロロアセチル－3，3，8a－トリメチルペルヒドロピロロ［1，2－a］ピリミジン－6－オン）、
「フリラゾール」または「MON 13900」（（RS）－3－ジクロロアセチル－5－（2－フリル）－2，2－ジメチルオキサゾリジン）（S3－10）；およびその（R）異性体（S3－11）。 S3) Compound of formula (S3)

Here, symbols and exponents are defined as follows:
R _C ¹ is (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₂ -C ₄ )-alkenyl, (C ₂ -C ₄ )-haloalkenyl, (C ₃ -C ₇ ) - represents cycloalkyl, preferably dichloromethyl;
R _C ² and R _C ³ are the same or different, hydrogen, (C ₁ -C ₄ )-alkyl, (C ₂ -C ₄ )-alkenyl, (C ₂ -C ₄ )-alkynyl, (C ₁ - C ₄ )-haloalkyl, (C ₂ -C ₄ )-haloalkenyl, (C ₁ -C ₄ )-alkylcarbamoyl-(C ₁ -C ₄ )-alkyl, (C ₂ -C ₄ )-alkenylcarbamoyl-( C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl, dioxolanyl-(C ₁ -C ₄ )-alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, represents substituted or unsubstituted phenyl, or R _C ² and R _C ³ together form a substituted or unsubstituted heterocycle, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring do;
Preferably:
Dichloroacetamide-type active compounds frequently used as pre-emergence safeners (soil-acting safeners), such as “dichloramide” (N,N-diallyl-2,2-dichloroacetamide) (S3-1),
"R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (S3-2) manufactured by Stauffer,
"R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) (S3-3) manufactured by Stauffer,
"Benoxacol" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
"PPG-1292" (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) (S3-5) manufactured by PPG Industries,
“DKA-24” (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (S3-6) manufactured by Sagro-Chem,
"AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) (S3-7) from Nitrokemia or Monsanto,
"TI-35" (1-dichloroacetyl azepane) (S3-8) manufactured by TRI-Chemical RT,
"Diclonone" (dicyclonon) or "BAS145138" or "LAB145138" (S3-9)
((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) from BASF,
“Furirazole” or “MON 13900” ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10); and its (R) isomer (S3-11 ).

（式中、記号および指数は以下の通り定義される：
A_DはSO₂－NR_D ³－COまたはCO－NR_D ³－SO₂を表し、
X_DはCHまたはNを表し；
R_D ¹はCO－NR_D ⁵R_D ⁶またはNHCO－R_D ⁷を表し；
R_D ²はハロゲン、（C₁～C₄）－ハロアルキル、（C₁～C₄）－ハロアルコキシ、ニトロ、（C₁～C₄）－アルキル、（C₁～C₄）－アルコキシ、（C₁～C₄）－アルキルスルホニル、（C₁～C₄）－アルコキシカルボニルまたは（C₁～C₄）－アルキルカルボニルを表し；
R_D ³は水素、（C₁～C₄）－アルキル、（C₂～C₄）－アルケニルまたは（C₂～C₄）－アルキニルを表し；
R_D ⁴はハロゲン、ニトロ、（C₁～C₄）－アルキル、（C₁～C₄）－ハロアルキル、（C₁～C₄）－ハロアルコキシ、（C₃～C₆）－シクロアルキル、フェニル、（C₁～C₄）－アルコキシ、シアノ、（C₁～C₄）－アルキルチオ、（C₁～C₄）－アルキルスルフィニル、（C₁～C₄）－アルキルスルホニル、（C₁～C₄）－アルコキシカルボニルまたは（C₁～C₄）－アルキルカルボニルを表し；
R_D ⁵は水素、（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₂～C₆）－アルケニル、（C₂～C₆）－アルキニル、（C₅～C₆）－シクロアルケニル、フェニルまたは窒素、酸素および硫黄からなる群のv_Dヘテロ原子を含有する3～6員ヘテロシクリルを表し、ここで、これらの後の7つの基は、ハロゲン、（C₁～C₆）－アルコキシ、（C₁～C₆）－ハロアルコキシ、（C₁～C₂）－アルキルスルフィニル、（C₁～C₂）－アルキルスルホニル、（C₃～C₆）－シクロアルキル、（C₁～C₄）－アルコキシカルボニル、（C₁～C₄）－アルキルカルボニルおよびフェニル、ならびに環状基の場合、また（C₁～C₄）－アルキルおよび（C₁～C₄）－ハロアルキルからなる群のv_D置換基によって置換されており；
R_D ⁶は水素、（C₁～C₆）－アルキル、（C₂～C₆）－アルケニルまたは（C₂～C₆）－アルキニルを表し、ここで、これらの後の3つの基は、ハロゲン、ヒドロキシ、（C₁～C₄）－アルキル、（C₁～C₄）－アルコキシおよび（C₁～C₄）－アルキルチオからなる群のv_D基によって置換されているか、あるいは
R_D ⁵とR_D ⁶がこれらを有する窒素原子と一緒になって、ピロリジニルまたはピペリジニル基を形成し；
R_D ⁷は水素、（C₁～C₄）－アルキルアミノ、ジ－（C₁～C₄）－アルキルアミノ、（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキルを表し、ここで、これらの後の2つの基は、ハロゲン、（C₁～C₄）－アルコキシ、（C₁～C₆）－ハロアルコキシおよび（C₁～C₄）－アルキルチオ、ならびに環状基の場合、また（C₁～C₄）－アルキルおよび（C₁～C₄）－ハロアルキルからなる群のv_D置換基によって置換されており；
n_Dは0、1または2を表し；
m_Dは1または2を表し；
v_Dは0、1、2または3を表す）；
これらのうち、例えば、国際公開第97／45016号から公知の、例えば以下の式（S4^a）のN－アシルスルホンアミド型の化合物

（式中、
R_D ⁷は（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキルを表し、ここで、これらの後の2つの基は、ハロゲン、（C₁～C₄）－アルコキシ、（C₁～C₆）－ハロアルコキシおよび（C₁～C₄）－アルキルチオ、ならびに環式基の場合、また（C₁～C₄）－アルキルおよび（C₁～C₄）－ハロアルキルからなる群のv_D置換基によって置換されており；
R_D ⁴はハロゲン、（C₁～C₄）－アルキル、（C₁～C₄）－アルコキシ、CF₃を表し；
m_Dは1または2を表し；
v_Dは0、1、2、または3を表す）
およびまた
例えば、国際公開第99／16744号から知られている、例えば以下の式（S4^b）のアシルスルファモイルベンズアミド

例えば、
R_D ⁵＝シクロプロピルおよび（R_D ⁴）＝2－OMe（「シプロスルファミド」、S4－1）、
R_D ⁵＝シクロプロピルおよび（R_D ⁴）＝5－Cl－2－OMe（S4－2）、
R_D ⁵＝エチルおよび（R_D ⁴）＝2－OMe（S4－3）、
R_D ⁵＝イソプロピルおよび（R_D ⁴）＝5－Cl－2－OMe（S4－4）および
R_D ⁵＝イソプロピルおよび（R_D ⁴）＝2－OMe（S4－5）
であるもの、およびまた
例えば、欧州特許第365484号から知られている、式（S4^c）のN－アシルスルファモイルフェニル尿素型の化合物

（式中、
R_D ⁸およびR_D ⁹は互いに独立に、水素、（C₁～C₈）－アルキル、（C₃～C₈）－シクロアルキル、（C₃～C₆）－アルケニル、（C₃～C₆）－アルキニルを表し、
R_D ⁴はハロゲン、（C₁～C₄）－アルキル、（C₁～C₄）－アルコキシ、CF₃を表し、
m_Dは1または2を表す）；
例えば
1－［4－（N－2－メトキシベンゾイルスルファモイル）フェニル］－3－メチル尿素、
1－［4－（N－2－メトキシベンゾイルスルファモイル）フェニル］－3，3－ジメチル尿素、
1－［4－（N－4，5－ジメチルベンゾイルスルファモイル）フェニル］－3－メチル尿素、
およびまた
例えば、中国特許第101838227号明細書から知られている、式（S4^d）のN－フェニルスルホニルテレフタルアミド

例えば、
R_D ⁴がハロゲン、（C₁～C₄）－アルキル、（C₁～C₄）－アルコキシ、CF₃を表し；
m_Dが1または2を表し；
R_D ⁵が水素、（C₁～C₆）－アルキル、（C₃～C₆）－シクロアルキル、（C₂～C₆）－アルケニル、（C₂～C₆）－アルキニル、（C₅～C₆）－シクロアルケニルを表す
もの。 S4) N-acylsulfonamide of formula (S4) and its salt,

(where the symbols and exponents are defined as follows:
A _D represents SO ₂ -NR _D ³ -CO or CO-NR _D ³ -SO ₂ ,
X _D represents CH or N;
R _D ¹ represents CO-NR _D ⁵ R _D ⁶ or NHCO-R _D ⁷ ;
R _D ² is halogen, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-haloalkoxy, nitro, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, ( Represents C ₁ -C ₄ )-alkylsulfonyl, (C ₁ -C ₄ )-alkoxycarbonyl or (C ₁ -C ₄ )-alkylcarbonyl;
R _D ³ represents hydrogen, (C ₁ -C ₄ )-alkyl, (C ₂ -C ₄ )-alkenyl or (C ₂ -C ₄ )-alkynyl;
R _D ⁴ is halogen, nitro, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-haloalkoxy, (C ₃ -C ₆ )-cycloalkyl, Phenyl, (C ₁ -C ₄ )-alkoxy, cyano, (C ₁ -C ₄ )-alkylthio, (C ₁ -C ₄ )-alkylsulfinyl, (C ₁ -C ₄ )-alkylsulfonyl, (C 1 -C ₄ )-alkyl C ₄ )-alkoxycarbonyl or (C ₁ to C ₄ )-alkylcarbonyl;
R _D ⁵ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₅ ~C ₆ )-represents cycloalkenyl, phenyl or a 3- to 6-membered heterocyclyl containing a v _D heteroatom of the group consisting of nitrogen, oxygen and sulfur, where these latter seven groups are halogen, (C ₁ to C ₆ )-alkoxy, (C ₁ to C ₆ )-haloalkoxy, (C ₁ to C ₂ )-alkylsulfinyl, (C ₁ to C ₂ )-alkylsulfonyl, (C ₃ to C ₆ )-cyclo Alkyl, (C ₁ -C ₄ )-alkoxycarbonyl, (C ₁ -C ₄ )-alkylcarbonyl and phenyl, and in the case of cyclic groups, also (C ₁ -C ₄ )-alkyl and (C ₁ -C ₄ ) - substituted by a v _D substituent of the group consisting of haloalkyl;
R _D ⁶ represents hydrogen, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl or (C ₂ -C ₆ )-alkynyl, where these latter three groups are substituted by a v _D group of the group consisting of halogen, hydroxy, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy and (C ₁ -C ₄ )-alkylthio, or
R _D ⁵ and R _D ⁶ together with the nitrogen atom containing them form a pyrrolidinyl or piperidinyl group;
R _D ⁷ is hydrogen, (C ₁ -C ₄ )-alkylamino, di-(C ₁ -C ₄ )-alkylamino, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl , where these latter two groups are halogen, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₆ )-haloalkoxy and (C ₁ -C ₄ )-alkylthio, and cyclic is also substituted by a v _D substituent of the group consisting of (C ₁ -C ₄ )-alkyl and (C ₁ -C ₄ )-haloalkyl;
n _D represents 0, 1 or 2;
m _D represents 1 or 2;
v _D represents 0, 1, 2 or 3);
Among these, for example, the N-acylsulfonamide type compound of the following formula (S4 ^a ), which is known from WO 97/45016

(In the formula,
R _D ⁷ represents (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, where these latter two groups are halogen, (C ₁ -C ₄ )-alkoxy , (C ₁ -C ₆ )-haloalkoxy and (C ₁ -C ₄ )-alkylthio, and in the case of cyclic groups, also from (C ₁ -C ₄ )-alkyl and (C ₁ -C ₄ )-haloalkyl. substituted by a v _D substituent of the group;
R _D ⁴ represents halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, CF ₃ ;
m _D represents 1 or 2;
v _D represents 0, 1, 2, or 3)
and also acylsulfamoylbenzamides, e.g. of formula (S4 ^b ), known e.g. from WO 99/16744:

for example,
R _D ⁵ = cyclopropyl and (R _D ⁴ ) = 2-OMe (“cyprosulfamide”, S4-1),
R _D ⁵ = cyclopropyl and (R _D ⁴ ) = 5-Cl-2-OMe(S4-2),
R _D ⁵ = ethyl and (R _D ⁴ ) = 2-OMe(S4-3),
R _D ⁵ = isopropyl and (R _D ⁴ ) = 5-Cl-2-OMe(S4-4) and
R _D ⁵ = Isopropyl and (R _D ⁴ ) = 2-OMe(S4-5)
and also compounds of the N-acylsulfamoylphenyl urea type of formula (S4 ^c ), known for example from EP 365 484.

(In the formula,
R _D ⁸ and R _D ⁹ are each independently hydrogen, (C ₁ -C ₈ )-alkyl, (C ₃ -C ₈ )-cycloalkyl, (C ₃ -C ₆ )-alkenyl, (C ₃ -C ₆ ) - represents alkynyl,
R _D ⁴ represents halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, CF ₃ ;
m _D represents 1 or 2);
for example
1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,
1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,
1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,
and also N-phenylsulfonyl terephthalamide of formula (S4 ^d ), known for example from China Patent No. 101838227

for example,
R _D ⁴ represents halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy, CF ₃ ;
m _D represents 1 or 2;
R _D ⁵ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₅ ～C ₆ )-Represents cycloalkenyl.

S5) active compounds of the class of hydroxyaromatic and aromatic-aliphatic carboxylic acid derivatives (S5), such as those described in WO 2004/084631, WO 2005/015994, WO 2005/016001; ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid.

S6) Active compounds of the class of 1,2-dihydroquinoxalin-2-ones (S6), for example 1-methyl-3-(2-thienyl)-1,2- as described in WO 2005/112630 Dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2 -dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one.

（式中、記号および指数は以下の通り定義される：
R_E ¹、R_E ²は互いに独立に、ハロゲン、（C₁～C₄）－アルキル、（C₁～C₄）－アルコキシ、（C₁～C₄）－ハロアルキル、（C₁～C₄）－アルキルアミノ、ジ－（C₁～C₄）－アルキルアミノ、ニトロであり；
A_EはCOOR_E ³またはCOSR_E ⁴を表し、
R_E ³、R_E ⁴は互いに独立に、水素、（C₁～C₄）－アルキル、（C₂～C₆）－アルケニル、（C₂～C₄）－アルキニル、シアノアルキル、（C₁～C₄）－ハロアルキル、フェニル、ニトロフェニル、ベンジル、ハロベンジル、ピリジニルアルキルおよびアルキルアンモニウムを表し、
n_E ¹は0または1を表し、
n_E ²、n_E ³は互いに独立に、0、1または2を表す）
好ましくは：
ジフェニルメトキシ酢酸、
エチルジフェニルメトキシアセテート、
メチルジフェニルメトキシアセテート（CAS登録番号41858－19－9）（S7－1）。 S7) Compound of formula (S7) described in International Publication No. 1998/38856,

(where the symbols and exponents are defined as follows:
R _E ¹ and R _E ² each independently represent halogen, (C ₁ to C ₄ )-alkyl, (C ₁ to C ₄ )-alkoxy, (C ₁ to C ₄ )-haloalkyl, (C ₁ to C ₄ )-alkylamino, di-(C ₁ -C ₄ )-alkylamino, nitro;
A _E stands for COOR _E ³ or COSR _E ⁴ ;
R _E ³ and R _E ⁴ each independently represent hydrogen, (C ₁ -C ₄ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₄ )-alkynyl, cyanoalkyl, (C ₁ ~C ₄ )-represents haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium;
n _E ¹ represents 0 or 1,
n _E ² , n _E ³ independently represent 0, 1 or 2)
Preferably:
diphenylmethoxyacetic acid,
ethyldiphenylmethoxyacetate,
Methyldiphenylmethoxyacetate (CAS Registration Number 41858-19-9) (S7-1).

（式中、
X_FはCHまたはNを表し、
n_Fは、X_F＝Nの場合、0～4の整数を表し、
X_F＝CHの場合、0～5の整数を表し、
R_F ¹はハロゲン、（C₁～C₄）－アルキル、（C₁～C₄）－ハロアルキル、（C₁～C₄）－アルコキシ、（C₁～C₄）－ハロアルコキシ、ニトロ、（C₁～C₄）－アルキルチオ、（C₁～C₄）－アルキルスルホニル、（C₁～C₄）－アルコキシカルボニル、場合により置換されたフェニル、場合により置換されたフェノキシを表し、
R_F ²は水素または（C₁～C₄）－アルキルを表し、
R_F ³は水素、（C₁～C₈）－アルキル、（C₂～C₄）－アルケニル、（C₂～C₄）－アルキニルまたはアリールを表し、上記の各炭素含有基の各々は非置換である、または1つもしくは複数の、好ましくは最大3つの、ハロゲンおよびアルコキシからなる群から選択される同一のもしくは異なる基によって置換されている）
またはその塩、
好ましくは、
X_FがCHを表し、
n_Fが0～2の整数を表し、
R_F ¹がハロゲン、（C₁～C₄）－アルキル、（C₁～C₄）－ハロアルキル、（C₁～C₄）－アルコキシ、（C₁～C₄）－ハロアルコキシを表し、
R_F ²が水素または（C₁～C₄）－アルキルを表し、
R_F ³が水素、（C₁～C₈）－アルキル、（C₂～C₄）－アルケニル、（C₂～C₄）－アルキニルまたはアリールを表し、上記の炭素含有基の各々が非置換である、または1つもしくは複数の、好ましくは最大3つの、ハロゲンおよびアルコキシからなる群の同一のもしくは異なる基によって置換されている、
化合物またはその塩。 S8) Compound of formula (S8) described in International Publication No. 98/27049,

(In the formula,
X _F represents CH or N,
n _F represents an integer from 0 to 4 when X _F = N,
If X _F = CH, it represents an integer from 0 to 5,
R _F ¹ is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy, nitro, ( C ₁ -C ₄ )-alkylthio, (C ₁ -C ₄ )-alkylsulfonyl, (C ₁ -C ₄ )-alkoxycarbonyl, optionally substituted phenyl, optionally substituted phenoxy,
R _F ² represents hydrogen or (C ₁ -C ₄ )-alkyl,
R _F ³ represents hydrogen, (C ₁ -C ₈ )-alkyl, (C ₂ -C ₄ )-alkenyl, (C ₂ -C ₄ )-alkynyl or aryl, and each of the above carbon-containing groups is a non-carbon group. or by one or more, preferably up to three, identical or different groups selected from the group consisting of halogen and alkoxy)
or its salt;
Preferably,
X _F represents CH,
n _F represents an integer from 0 to 2,
R _F ¹ represents halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy,
R _F ² represents hydrogen or (C ₁ -C ₄ )-alkyl,
R _F ³ represents hydrogen, (C ₁ -C ₈ )-alkyl, (C ₂ -C ₄ )-alkenyl, (C ₂ -C ₄ )-alkynyl or aryl, and each of the above carbon-containing groups is unsubstituted. or substituted by one or more, preferably up to three, identical or different groups of the group consisting of halogen and alkoxy,
compound or its salt.

S9) Active compounds of the class of 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example 1,2-dihydro-4-hydroxy-1- as described in WO 1999/000020 Ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS registration number 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl) )-2-quinolone (CAS registration number 95855-00-8).

（式中、
R_G ¹はハロゲン、（C₁～C₄）－アルキル、メトキシ、ニトロ、シアノ、CF₃、OCF₃を表し、
Y_G、Z_Gは互いに独立に、OまたはSを表し、
n_Gは0～4の整数を表し、
R_G ²は（C₁～C₁₆）－アルキル、（C₂～C₆）－アルケニル、（C₃～C₆）－シクロアルキル、アリール；ベンジル、ハロベンジルを表し、
R_G ³は水素または（C₁～C₆）－アルキルを表す）。 S10) Described in International Publication No. 2007/023719 and International Publication No. 2007/023764,
Compound of formula (S10 ^a ) or (S10 ^b )

(In the formula,
R _G ¹ represents halogen, (C ₁ -C ₄ )-alkyl, methoxy, nitro, cyano, CF ₃ , OCF ₃ ;
Y _G and Z _G independently represent O or S,
n _G represents an integer from 0 to 4,
R _G ² represents (C ₁ -C ₁₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₃ -C ₆ )-cycloalkyl, aryl; benzyl, halobenzyl;
R _G ³ represents hydrogen or (C ₁ -C ₆ )-alkyl).

S11) Active compounds of the oximino compound type, known as seed dressing agents (S11), such as "Oxabetrinil" ((Z)-1,3), known as seed dressing safeners of millet/sorghum against metolachlor damage. -dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1),
“Fluxofenim” (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolane) is known as a millet/sorghum seed dressing safener against metolachlor damage. -2-ylmethyl)oxime) (S11-2), and “cyometrinil” or “CGA-43089” ((Z)-cyanomethoxyimino ( phenyl)acetonitrile) (S11-3).

S12) Active compounds of the class of isothiochromanones (S12), such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]cetate (CAS Registry No. 205121-04-6) (S12 -1) and related compounds of International Publication No. 1998/13361.

One or more compounds of group (S13):
"Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a corn seed dressing chemical damage reducer for damage caused by thiocarbamate herbicides;
"Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as a phytotoxic agent for pretilachlor in sown rice,
“Flurazole” (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13- 3),
"CL 304415" (CAS registration number 31541-57-8) manufactured by American Cyanamid, known as a corn phytotoxic agent for damage caused by imidazolinones
(4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4),
"MG 191" (CAS registration number 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) manufactured by Nitrokemia, known as a corn phytotoxicity reducer,
“MG 838” manufactured by Nitrokemia (CAS registration number 133993-74-5)
(2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6),
"Disulfoton" (O, O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7),
"Dietolate" (O, O-diethyl O-phenyl phosphorothioate) (S13-8),
"Mephenate" (4-chlorophenylmethyl carbamate) (S13-9).

S14) In addition to herbicidal activity against harmful plants, active compounds also have phytotoxic activity on crop plants such as rice, such as ``dimepiperate'' or ``MY 93'', which is known as a phytotoxic agent for rice against damage caused by the herbicide molinate. (S-1-methyl 1-phenylethylpiperidine-1-carbothioate),
"Daimeron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), known as a rice phytotoxic agent for damage caused by thiometrinylimazosulfuron herbicide;
``Cumiluron'' = ``JC 940'' (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl) urea), known as a rice phytotoxicity reducer against damage caused by certain herbicides, JP-A-Sho 60087254),
``Methoxyphenone'' or ``NK 049''(3,3'-dimethyl-4-methoxybenzophenone), known as a rice phytotoxic agent against damage caused by certain herbicides;
"CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) (CAS registration number 54091-06-4) manufactured by Kumiai is known as a phytotoxic agent for damage caused by certain herbicides in rice.

（式中、
R_H ¹は（C₁～C₆）－ハロアルキル基を表し、
R_H ²は水素またはハロゲンを表し、
R_H ³、R_H ⁴は互いに独立に、水素、（C₁～C₁₆）－アルキル、（C₂～C₁₆）－アルケニルまたは（C₂～C₁₆）－アルキニル、
（ここで、これらの後の3つの基の各々は非置換である、またはハロゲン、ヒドロキシル、シアノ、（C₁～C₄）－アルコキシ、（C₁～C₄）－ハロアルコキシ、（C₁～C₄）－アルキルチオ、（C₁～C₄）－アルキルアミノ、ジ［（C₁～C₄）－アルキル］アミノ、［（C₁～C₄）－アルコキシ］カルボニル、［（C₁～C₄）－ハロアルコキシ］カルボニル、非置換もしくは置換（C₃～C₆）－シクロアルキル、非置換もしくは置換フェニル、非置換もしくは置換ヘテロシクリルの群の1つもしくは複数の基によって置換されている）、
または（C₃～C₆）－シクロアルキル、（C₄～C₆）－シクロアルケニル、環の片側で4～6員飽和もしくは不飽和炭素環式環と融合した（C₃～C₆）－シクロアルキル、または環の片側で4～6員飽和もしくは不飽和炭素環式環と融合した（C₄～C₆）－シクロアルケニル
（ここで、これらの後の4つの基の各々は、非置換である、またはハロゲン、ヒドロキシル、シアノ、（C₁～C₄）－アルキル、（C₁～C₄）－ハロアルキル、（C₁～C₄）－アルコキシ、（C₁～C₄）－ハロアルコキシ、（C₁～C₄）－アルキルチオ、（C₁～C₄）－アルキルアミノ、ジ［（C₁～C₄）－アルキル］アミノ、［（C₁～C₄）－アルコキシ］カルボニル、［（C₁～C₄）－ハロアルコキシ］カルボニル、非置換もしくは置換（C₃～C₆）－シクロアルキル、非置換もしくは置換フェニル、および非置換もしくは置換ヘテロシクリルからなる群の1つもしくは複数の基によって置換されている）
を表す、
あるいは
R_H ³は（C₁～C₄）－アルコキシ、（C₂～C₄）－アルケニルオキシ、（C₂～C₆）－アルキニルオキシまたは（C₂～C₄）－ハロアルコキシを表し、
R_H ⁴は水素または（C₁～C₄）－アルキルを表す、あるいは
R_H ³およびR_H ⁴は、直接結合した窒素原子と一緒になって、窒素原子と同様に、さらなる環ヘテロ原子、好ましくは最大2個のN、OおよびSの群のさらなる環ヘテロ原子を含有してもよく、非置換である、またはハロゲン、シアノ、ニトロ、（C₁～C₄）－アルキル、（C₁～C₄）－ハロアルキル、（C₁～C₄）－アルコキシ、（C₁～C₄）－ハロアルコキシおよび（C₁～C₄）－アルキルチオの群の1つもしくは複数の基によって置換された4～8員複素環式環を表す）。 S15) Described in International Publication No. 2008/131861 and International Publication No. 2008/131860,
Compound of formula (S15) or its tautomer

(In the formula,
R _H ¹ represents a (C ₁ -C ₆ )-haloalkyl group,
R _H2 represents hydrogen or ^halogen ;
R _H ³ and R _H ⁴ each independently represent hydrogen, (C ₁ -C ₁₆ )-alkyl, (C ₂ -C ₁₆ )-alkenyl or (C ₂ -C ₁₆ )-alkynyl,
(wherein each of these latter three groups is unsubstituted or halogen, hydroxyl, cyano, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy, (C ₁ ~C ₄ )-alkylthio, (C ₁ ~C ₄ )-alkylamino, di[(C ₁ ~C ₄ )-alkyl]amino, [(C ₁ ~C ₄ )-alkoxy]carbonyl, [(C ₁ ~ C ₄ )-haloalkoxy]carbonyl, unsubstituted or substituted (C ₃ -C ₆ )-cycloalkyl, unsubstituted or substituted phenyl, unsubstituted or substituted by one or more groups of the group heterocyclyl) ,
or (C ₃ -C ₆ )-cycloalkyl, (C ₄ -C ₆ )-cycloalkenyl, (C ₃ -C ₆ )- fused to a 4- to 6-membered saturated or unsaturated carbocyclic ring on one side of the ring. cycloalkyl, or (C ₄ -C ₆ )-cycloalkenyl fused to a 4- to 6-membered saturated or unsaturated carbocyclic ring on one side of the ring, where each of these latter four groups is an unsubstituted or halogen, hydroxyl, cyano, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy , (C ₁ -C ₄ )-alkylthio, (C ₁ -C ₄ )-alkylamino, di[(C ₁ -C ₄ )-alkyl]amino, [(C ₁ -C ₄ )-alkoxy]carbonyl, [ (C ₁ -C ₄ )-haloalkoxy]carbonyl, unsubstituted or substituted (C ₃ -C ₆ )-cycloalkyl, unsubstituted or substituted phenyl, and unsubstituted or substituted heterocyclyl. )
represents,
or
R _H ³ represents (C ₁ -C ₄ )-alkoxy, (C ₂ -C ₄ )-alkenyloxy, (C ₂ -C ₆ )-alkynyloxy or (C ₂ -C ₄ )-haloalkoxy,
R _H ⁴ represents hydrogen or (C ₁ -C ₄ )-alkyl, or
R _H ³ and R _H ⁴ together with the directly bonded nitrogen atom contain, like the nitrogen atom, a further ring heteroatom, preferably up to two further ring heteroatoms of the group N, O and S. may contain unsubstituted or halogen, cyano, nitro, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ - _C4 )-haloalkoxy and ( _C1 - _C4 )-alkylthio).

S16) Active compounds that are mainly used as herbicides but also have safener action on crop plants, such as (2,4-dichlorophenoxy)acetic acid (2,4-D),
(4-chlorophenoxy)acetic acid,
(R,S)-2-(4-chloro-o-tolyloxy)propionic acid (Mecoprop),
4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),
(4-chloro-o-tolyloxy)acetic acid (MCPA),
4-(4-chloro-o-tolyloxy)butyric acid,
4-(4-chlorophenoxy)butyric acid,
3,6-dichloro-2-methoxybenzoic acid (dicamba),
1-(Ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro-ethyl).

Particularly preferred safeners are, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and dichlormide.

Wettable powders are preparations that are homogeneously dispersible in water and contain, in addition to the active compound, surfactants (wetting agents, dispersing agents) of ionic and/or nonionic type, apart from diluents or inert substances. agents), such as polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonates, 2,2'- Also included are sodium dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate. To prepare the wettable powders, the herbicidally active compounds are finely ground in customary equipment, such as, for example, hammer mills, blow mills and air jet mills, and simultaneously or subsequently mixed with formulation auxiliaries.

Emulsions are prepared by combining the active compounds in organic solvents, such as butanol, cyclohexanone, dimethylformamide, xylene or relatively high-boiling aromatic or carbonized solvents, with the addition of one or more ionic and/or nonionic surfactants (emulsifiers). Produced by dissolving in hydrogen or a mixture of organic solvents. Examples of emulsifiers that may be used are calcium alkylaryl sulfonates (such as calcium dodecylbenzenesulfonate), or nonionic emulsifiers (fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide). condensates, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters.

Dust products are obtained by grinding the active compounds with finely dispersed solids, for example talc, natural clays (such as kaolin, bentonite and pyrophyllite) or diatomaceous earth.

The suspending agent may be aqueous or oil-based. These can be prepared, for example, by wet milling using a commercially available bead mill and optionally adding, for example, surfactants already listed above for other formulation types.

Emulsion formulations, e.g. oil-in-water emulsion formulations (EW), can be prepared using a stirrer, a colloid mill and/or a static It can be manufactured using a commercial mixer.

Granules can be prepared by spraying the active compound onto a granular inert material capable of adsorbing it or by applying the active compound concentrate to a carrier material (sand, sand, etc.) using an adhesive, for example polyvinyl alcohol, sodium polyacrylate or mineral oil. (such as kaolinite or granular inert materials). If desired as a mixture with fertilizers, suitable active compounds can also be granulated in the manner customary for the production of fertilizer granules.

Granule wettable powders are generally prepared by conventional methods such as spray drying, fluidized granulation, pan granulation, high speed mixer mixing, and extrusion without solid inert materials.

For the manufacture of pans, fluidized beds, extruders and spray granules, see, for example, "Spray-Drying Handbook" 3rd edition 1979, G. Goodwin Ltd. , London, J. E. Browning, "Agglomeration", Chemical and Engineering 1967, pp. 147ff; see methods in "Perry's Chemical Engineer's Handbook", 5th edition, McGraw Hill, New York 1973, pp. 8-57.

For further details regarding the formulation of crop protection compositions, see, for example, G. C. Klingman, “Weed Control as a Science,” John Wiley and Sons, Inc. , New York, 1961, pp. 81-96 and J. D. Freyer, S. A. See Evans, Weed Control Handbook, 5th edition, Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

Agrochemical formulations generally contain from 0.1% to 99% by weight, in particular from 0.1% to 95% by weight, of the compounds of the invention. In wettable powders, the active compound concentration is, for example, from about 10% to 90% by weight, with the balance consisting of customary formulation ingredients up to 100% by weight. In emulsions, the active compound concentration may be from about 1% to 90% by weight, preferably from 5% to 80%. Preparations in powder form contain from 1% to 30% by weight of active compound, preferably usually from 5% to 20% by weight; spray solutions contain about 0.05% to 80% by weight, preferably Contains from 2% to 50% by weight of active compound. In the case of wettable powders, the active compound content depends in part on whether the active compound is in liquid or solid form and on which granulation aids, fillers, etc. are used. In hydrated granules, the content of active compound is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.

Furthermore, the active compound formulations mentioned may optionally include the respective customary spreading agents, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, Contains antifoaming agents, evaporation inhibitors and agents that affect pH and viscosity.

Based on these formulations, combinations with other insecticidal active substances, such as insecticides, acaricides, herbicides, fungicides, as well as safeners, fertilizers and/or growth regulators, can be added, for example to the final formulation. It is also possible to produce it in the form of or as a tank mix.

For application, the preparations in commercially available form are diluted, if appropriate, in the customary manner with water, for example in the case of wettable powders, emulsions, dispersions and wettable powders. Powder formulations, granules for soil application or scattering and spray solutions are usually not further diluted with other inert substances before application.

The required application rate of the compound of formula (I) will vary depending on external conditions including, inter alia, temperature, humidity and the type of herbicide used. This can vary within a wide range, for example from 0.001 to 1.0 kg/ha or more of active substance, but preferably from 0.005 to 750 g/ha.

Carriers are natural or synthetic organic or inorganic substances with which the active compounds are mixed or combined for good applicability, in particular for application to plants or plant parts or seeds. The carrier may be solid or liquid and should generally be inert and suitable for agricultural use.

Useful solid or liquid carriers include, for example, ammonium salts and natural rock powders such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock powders such as finely divided silica, alumina and natural or synthetic silicates. Included are salts, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral and vegetable oils and derivatives thereof. It is likewise possible to use mixtures of such carriers. Solid carriers useful for granules include, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic coarse powders, as well as granules of organic materials, such as sawdust, Also included are coconut husks, corn cobs and tobacco stalks.

Suitable liquefied gas bulking agents or carriers are liquids that are gases at standard temperature and atmospheric pressure, such as halogenated hydrocarbons, or aerosol propellants such as butane, propane, nitrogen and carbon dioxide.

In the formulation, adhesives are used, such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or natural phospholipids, such as cephalin and lecithin, and synthetic phospholipids. Is possible. Further additives may be mineral and vegetable oils.

If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Useful liquid solvents are essentially aromatic such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or dichloromethane, aliphatic hydrocarbons such as cyclohexane or Paraffins such as mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. It is.

The compositions of the invention may further include further ingredients, such as surfactants. Useful surfactants are emulsifiers and/or foam formers, dispersants or wetting agents having ionic or nonionic properties, or mixtures of these surfactants. Examples are salts of polyacrylic acids, salts of lignosulfonic acids, salts of phenolsulfonic acids or naphthalenesulfonic acids, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty amines, substituted phenols (preferably alkylphenols or arylphenols). phenol), salts of sulfosuccinates, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and compounds containing sulfuric acid esters, sulfonic acid esters and phosphoric acid esters derivatives such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignosulfite waste liquors and methylcellulose. The presence of a surfactant is necessary if one of the active compounds and/or one of the inert carriers is insoluble in water and the application is carried out in water. The proportion of surfactants is from 5 to 40% by weight of the composition according to the invention. Inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. It is possible to use dyes.

If appropriate, other additional ingredients can also be present, such as, for example, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, sequestrants, complexing agents. be. In general, the active compounds can be combined with any solid or liquid additives commonly used for formulation purposes. Generally, the compositions and formulations of the invention are comprised between 0.05% and 99%, preferably between 0.01% and 98%, preferably between 0.1% and 95%, more preferably between 0.5% and 99% by weight. % to 90% by weight of active compound, most preferably 10% to 70% by weight. The active compounds or compositions of the invention can be used as such or depending on their respective physical and/or chemical properties to be used as aerosols, capsule suspensions, cold atomizers, hot atomizers, encapsulated granules, fine particles, etc. Granules, flowable concentrates for seed treatment, ready-to-use solutions, powders, emulsions, oil-in-water emulsions, water-in-oil emulsions, macrogranules, microgranules, oil-dispersible powders, oil-miscible flowables Concentrates, oil-miscible liquids, foams, pastes, pesticide-coated seeds, suspension concentrates, suspoemulsion concentrates, soluble concentrates, suspensions, sprayable powders, soluble powders, powders and granules, water-soluble granules or tablets, water-soluble powders for seed treatment, wettable powders, natural products and synthetic substances impregnated with active compounds, and microencapsulation in polymeric substances and coating materials for seeds, as well as ULV cold fog and It may be used in formulations or usage forms prepared therefrom, such as warm fog formulations.

The formulations mentioned are, for example, combining the active compound with at least one customary filler, solvent or diluent, emulsifying agent, dispersing agent and/or binder or fixing agent, wetting agent, water repellent, optionally a drying agent, and UV stabilizers, and optionally dyes and pigments, defoamers, preservatives, secondary thickeners, tackifiers, gibberellins and other processing aids, in a manner known per se. be able to.

The compositions of the invention include not only formulations that are ready for use and can be deployed with suitable equipment for plants or seeds, but also commercial concentrates that must be diluted with water before use.

The active compounds of the invention may be used as such, or in their (commercial standard) formulations, or as insecticides, attractants, sterilizers, fungicides, acaricides, nematicides, fungicides, growth regulators, They can be present in use forms prepared from these formulations as mixtures with other (known) active compounds such as herbicides, fertilizers, safeners or semiochemicals.

The treatment according to the invention of plants and plant parts with active compounds or compositions can be carried out using customary treatment methods, for example by dipping, spraying, atomizing, irrigation, evaporating, dusting, fogging, scattering, foaming, painting, spreading. , by watering (drench), drip irrigation, and in the case of propagation material, especially seeds, and also by coating, as powders for dry seed treatment, solutions for seed treatment, water-soluble powders for treatment of slurries, one or more This may be done directly or by acting on the surroundings, habitat or storage space, such as by coating with a coat. Furthermore, it is possible to apply the active compound by ultra-low volume methods or to inject the active compound formulation or the active compound itself into the soil.

Of particular interest is the treatment of transgenic seeds with the active compounds or compositions of the invention, as also described below. This relates to seeds of plants that contain at least one heterologous gene that allows the expression of a polypeptide or protein that has insecticidal properties. Heterologous genes in the transgenic seeds include, for example, Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus (Glomus) or from a microorganism of the species Gliocladium. The heterologous gene is preferably from a species of Bacillus, in which case the gene product is effective against corn borer larvae and/or western corn rootworm. The heterologous gene is more preferably derived from Bacillus thuringiensis.

In the context of the present invention, the compositions of the invention are applied to seeds alone or in suitable formulations. Preferably, the seeds are treated in a sufficiently stable state so that no damage occurs during the treatment process. Generally, seeds can be treated at any time between harvest and sowing. It is customary to use seeds that have been separated from the plant and freed from the cob, husk, stalk, skin, hair or pulp. For example, it is possible to use seeds that have been harvested, washed and dried to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seeds which, after drying, have been treated, for example with water, and then dried again.

In general, when treating seeds, it is ensured that the amount of the composition of the invention and/or further additives applied to the seeds is selected such that seed germination is not impaired and the resulting plants are not damaged. It must be. This must be ensured in particular in the case of active compounds which can exhibit phytotoxic effects at certain application rates.

The compositions of the invention can be applied directly, ie without other ingredients and undiluted. Generally, it is preferred to apply the composition to the seeds in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to the person skilled in the art and are described, for example, in the following documents: US Pat. No. 4,272,417, US Pat. No. 4,245,432, US Pat. No. 4,808,430. No. 5,876,739, US Patent Application Publication No. 2003/0176428, International Publication No. 2002/080675, International Publication No. 2002/028186.

The active compounds of the invention can also be converted into conventional seed coating formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seeds, and ULV formulations. I can do it.

These preparations combine the active compounds with customary additives, such as customary fillers and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives. It is prepared in a known manner by mixing the agent, gibberellin, and water.

Dyes that can be present in the seed dressing preparations that can be used according to the invention are all dyes that are customary for such purposes. It is possible to use either pigments that are poorly soluble in water or dyes that are soluble in water. Examples include Rhodamine B, C. I. Pigment Red 112 and C. I. One example is the dye known under the name Solvent Red 1.

Useful wetting agents which can be present in the seed dressing formulations usable according to the invention are all substances which promote wetting and are customary for the formulation of agrochemically active compounds. Alkylnaphthalene sulfonates, such as diisopropyl or diisobutylnaphthalene sulfonate, may preferably be used.

Suitable dispersants and/or emulsifiers which may be present in the seed dressing formulations usable according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemically active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants include, inter alia, ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, and phosphorylated or sulfated derivatives thereof. Suitable anionic dispersants are in particular lignosulfonates, polyacrylates and arylsulfonate-formaldehyde condensates.

Antifoams that can be present in the seed dressing preparations that can be used according to the invention are all foam inhibitors customary for the formulation of agrochemically active compounds. Silicone defoamers and magnesium stearate can preferably be used.

Preservatives that can be present in the seed dressing preparations that can be used according to the invention are all substances that can be used for this purpose in agrochemical compositions. Examples include dichlorophene and benzyl alcohol hemiformal.

Secondary thickeners that can be present in the seed dressing formulations that can be used according to the invention are all substances that can be used for this purpose in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.

Useful spreading agents that may be present in the seed coating formulations usable according to the invention are all customary binders that can be used in seed coating products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

The seed dressing formulations usable according to the invention can be used directly or after predilution with water for the treatment of a wide range of different seeds, including seeds of transgenic plants. In this case, further synergistic effects may occur in the interaction with the substances formed by expression.

For treating seeds with the seed dressing formulations usable according to the invention or preparations prepared therefrom by adding water, useful devices include all mixing devices conventionally used for seed dressings. be. Specifically, the seed dressing procedure involves placing the seeds in a mixer and adding a specific desired amount of the seed dressing formulation, either by itself or after pre-diluting with water, so that the formulation is homogeneously distributed over the seeds. These are mixed up to. If appropriate, this is followed by a drying operation.

In view of their good phytocompatibility, favorable warm-blooded animal toxicity and good environmental compatibility, the active compounds of the invention are suitable for protecting plants and plant organs, increasing yields and improving the quality of harvested crops. ing. These can preferably be used as crop protection agents. They are active against normally sensitive and resistant species and against all or specific stages of development.

Plants that can be treated according to the invention include the following major crop plants: corn, soybean, cotton, Brassica oilseeds, such as Brassica napus (e.g. canola), Brassica Brassica rapa, B. juncea (e.g. rapeseed) and Abyssinia carinata, rice, wheat, sugar beets, sugar cane, oats, rye, barley, millet and sorghum, triticale, flax, grapes and various various fruits and vegetables from the plant taxa of the Rosaceae species, such as pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, and strawberries, etc. Berries), Ribesioidae species, Juglandaceae species, Betulaceae species, Anacardiaceae species, Fagaceae species, Moraceae species, Oleaceae species ( Oleaceae species, Actinidaceae species, Lauraceae species, Musaceae species (e.g. banana trees and plantations), Rubiaceae species (e.g. coffee), Theaceae ) species, Sterculiceae species, Rutaceae species (e.g. lemons, oranges and grapefruits); Solanaceae species (e.g. tomatoes, potatoes, peppers, eggplants), Liliaceae species , Compositae species (e.g. lettuce, artichoke and chicory - including chicory root, endive or common chicory), Umbelliferae species (e.g. carrots, parsley, celery and celery root), Cucurbitaceae (Cucurbitaceae) species (e.g. cucumbers, including gherkins, pumpkins, watermelons, calabash and melons), Alliaceae (e.g. leeks and onions), Cruciferae species (e.g. white cabbage, Red cabbage, broccoli, cauliflower, Brussels sprouts, bok choy, radish, horseradish, watercress and Chinese cabbage), Leguminosae species (e.g. peanuts, peas and beans, e.g. safflower and broad beans), Chenopodiaceae ) species (e.g. Swiss chard, forage beet, spinach, beet root), Malvaceae species (e.g. okra), Asparagaceae (e.g. asparagus); useful garden and forest plants and ornamentals plants; as well as genetically modified versions of these plants in each case.

As mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding techniques such as hybridization or protoplast fusion, and parts thereof are treated. In a further preferred embodiment, transgenic plants and plant cultivars, or parts thereof, obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetic recombinants), are treated. The term "part" or "part of a plant" or "plant part" has been explained above. According to the invention, it is particularly preferred to treat plants of the respective commercially conventional plant cultivars or those in use. Plant cultivars are understood to mean plants with new characteristics (“traits”) cultivated by conventional breeding, mutagenesis or recombinant DNA techniques. These can be cultivars, varieties, biotypes and genotypes.

The treatment method of the present invention can be used to treat genetically modified organisms (GMOs), such as plants or seeds. Genetically modified plants (or transgenic plants) are plants in which a foreign gene has been stably integrated into the genome. The term "heterologous gene" refers to a gene that is provided or assembled outside the plant and that, when introduced into the nuclear, chloroplast or mitochondrial genome, causes the expression of a protein or polypeptide of interest or into a transformed plant by down-regulating or switching off (e.g. by antisense, co-suppression or RNAi technology [RNA interference]) another gene present in the plant, or multiple other genes present in the plant. Essentially refers to a gene that confers a new or improved agronomic or other property. A heterologous gene located in the genome is also called a transgene. An introduced gene defined by its specific presence within the plant genome is called a transformation or transgenic event.

Depending on the plant species or plant cultivar, its location and growth conditions (soil, climate, vegetation period, diet), the treatments of the invention may also have a superadditive ("synergistic") effect. for example,
In fact, the following effects over and above the expected effects are possible: a reduction in the application rate and/or a broadening of the activity spectrum and/or an increase in the effectiveness of the active compounds and compositions that can be used according to the invention; Superior plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salinity, increased flowering performance, easier harvesting, accelerated ripening, higher yields, larger fruits, larger plants. height, greener leaf color, earlier flowering, higher quality and/or higher nutritional value of the harvested product, higher sugar concentration in the fruit, better storage stability and/or of the harvested product. Processability.

Plants and plant cultivars preferably treated according to the invention have genetic material that confers on these plants (even those obtained by breeding and/or biotechnological means) particularly advantageous and useful traits. Contains all plants.

Examples of nematode resistant plants include, for example, the following U.S. patent applications: No. 11/765,491; No. 11/765,494; No. 10/926,819; No. 10/782,020; 12/032,479, 10/783,417, 10/782,096, 11/657,964, 12/192,904, 11/396,808, 12/ No. 166, 253, No. 12/166, 239, No. 12/166, 124, No. 12/166, 209, No. 11/762, 886, No. 12/364, 335, No. 11/763, No. 947, No. 12/252,453, No. 12/209,354, No. 12/491,396 and No. 12/497,221.

Plants that can be treated according to the invention are generally hybrid plants that already exhibit properties of heterosis or hybrid effect resulting in high yield, vigor, good health and resistance to biotic and abiotic stress factors. Such plants are typically produced by crossing an inbred male sterile parental line (female breeding parent) with another inbred male fertile parental line (male breeding parent) . Hybrid seeds are typically harvested from male-sterile plants and sold to growers. Male-sterile plants are sometimes produced by detasseling (i.e., mechanical removal of male reproductive organs or male flowers) (e.g., in maize), but more typically male sterility is caused by Full recovery of male fertility in hybrid plants that are the result of genetic determinants, including genetic determinants responsible for male sterility, in which case, especially if seeds are the desired product harvested from the hybrid plants. It is typically beneficial to ensure that This can be achieved by ensuring that the male breeding parents have appropriate fertility restorer genes capable of restoring male fertility in hybrid plants containing the genetic determinants responsible for male sterility. can. Genetic determinants of male sterility may be located in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been described, for example, for Brassica species. However, genetic determinants of male sterility can also be located in the nuclear genome. Male sterile plants can also be obtained by plant biotechnology methods such as genetic engineering. A particularly useful means of obtaining male sterile plants is described in WO 89/10396, in which a ribonuclease such as, for example, barnase is selectively expressed in the tapetum cells of the stamens. Fertility can then be restored by expression in the tapetum cells of a ribonuclease inhibitor such as barstar.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. It is. Such plants can be obtained by genetic transformation or by selection of plants containing mutations conferring such herbicide tolerance.

The herbicide-tolerant plant is, for example, a glyphosate-tolerant plant, that is, a plant made tolerant to the herbicide glyphosate or a salt thereof. Plants can be made tolerant to glyphosate by a variety of methods. For example, glyphosate-tolerant plants can be obtained by transforming plants with a gene encoding the enzyme 5-enol-pyruvyl-shikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science, 221, 370-371), the bacterium Agrobacterium spp. CP4 gene (Barry et al., 1992, Curr. Topics Plant Physiol. 7, 139-145), petunia EPSPS (Shah et al., 1986, Science, 233, 478-481), tomato EPSPS (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289) or Eleusine EPSPS (WO 01/66704). It may be a mutant EPSPS. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding the glyphosate oxidoreductase enzyme. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding the glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants containing natural mutations of the above genes. Plants expressing the EPSPS gene that confer glyphosate tolerance have been described. Plants expressing other genes that confer glyphosate tolerance, such as decarboxylase genes, have been described.

Other herbicide-tolerant plants are plants made tolerant to herbicides that inhibit the enzyme glutamine synthase, such as bialaphos, phosphinothricin or glufosinate. Such plants can be obtained by expressing enzymes that detoxify herbicides or mutant forms of the glutamine synthase enzyme that are resistant to inhibition. An example of such an effective detoxifying enzyme is the enzyme encoding phosphinothricin acetyltransferase (such as the bar or pat protein of Streptomyces sp.). Plants expressing exogenous phosphinothricin acetyltransferase have been described.

Further herbicide-tolerant plants are also plants made tolerant to herbicides that inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). Hydroxyphenylpyruvate dioxygenase is an enzyme that catalyzes the reaction in which parahydroxyphenylpyruvate (HPP) is converted to homogentisic acid. Plants resistant to HPPD inhibitors can be found in WO 96/38567, WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387 or the US As described in Patent No. 6768044, it can be transformed with a gene encoding a naturally resistant HPPD enzyme, or a gene encoding a mutant or chimeric HPPD enzyme. Resistance to HPPD inhibitors can also be obtained by transforming plants with genes encoding certain enzymes that allow the formation of homogentisic acid despite inhibition of the natural HPPD enzyme by the HPPD inhibitor. Such plants are described in WO 99/34008 and WO 02/36787. As described in WO 2004/024928, plants can be made resistant to HPPD inhibitors by transforming them with a gene encoding a prephenate dehydrogenase enzyme in addition to a gene encoding an HPPD resistance enzyme. It can also improve tolerance. In addition, plants can be made more resistant to HPPD inhibitors by inserting into their genome genes encoding enzymes that metabolize or degrade HPPD inhibitors, such as CYP450 enzymes (International Publication No. 2007/2007). 103567 and International Publication No. 2008/150473).

Other herbicide-tolerant plants are those made tolerant to acetolactate synthase (ALS) inhibitors. Known ALS inhibitors include, for example, sulfonylureas, imidazolinones, triazolopyrimidines, pyrimidinyloxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinone herbicides. For example, as described in Tranel and Wright (Weed Science 2002, 50, 700-712), different mutations in the ALS enzyme (acetohydroxy acid synthase, also known as AHAS) are associated with different herbicides and groups of herbicides. It is known that it confers resistance to. The production of sulfonylurea- and imidazolinone-tolerant plants has been described. Additional sulfonylurea and imidazolinone resistant plants have also been described.

Additional plants resistant to imidazolinones and/or sulfonylureas can be obtained by mutagenesis, by selection of cell cultures in the presence of herbicides, or by mutation breeding (for example, soybeans have Patent No. 5,084,082, WO 97/41218 for rice, U.S. Pat. No. 5,773,702 and WO 99/057965 for sugar beet, U.S. Pat. , No. 599 or WO 01/065922 for sunflowers).

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be treated according to the invention are resistant to abiotic stress factors. Such plants can be obtained by genetic transformation or by selection of plants containing mutations conferring such stress tolerance. Particularly useful stress-tolerant plants include:
a. A plant containing a transgene capable of reducing the expression and/or activity of a poly(ADP-ribose) polymerase (PARP) gene in a plant cell or plant;
b. A plant comprising a stress tolerance-enhancing transgene capable of reducing the expression and/or activity of a PARG-encoding gene in a plant or plant cell;
c. Stress tolerance enhancer encoding plant functional enzymes of the nicotinamide adenine dinucleotide salvage biosynthetic pathway including nicotinamide amidase, nicotinate phosphoribosyltransferase, nicotinate mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase Plants containing the transgene.

Plants or plant cultivars (obtained by plant biotechnological methods, such as genetic engineering) which can also be treated according to the invention can be characterized by changes in the quantity, quality and/or storage stability of the harvested product and/or changes in the harvested product's quantity, quality and/or storage stability. Indicating a change in the properties of a particular component, e.g.:
1) Physicochemical properties, in particular amylose content or amylose/amylopectin ratio, degree of branching, average chain length, side chain distribution, viscosity behavior, gelling strength, starch granule size and/or starch granule morphology, are different from wild-type plant cells. or a transgenic plant that synthesizes a modified starch that has been altered compared to the synthetic starch in the plant, so that this modified starch is more suitable for certain uses.
2) Transgenic plants that synthesize non-starch carbohydrate polymers or that synthesize non-starch carbohydrate polymers that have altered properties compared to wild-type plants without genetic modification. Examples include plants producing polyfructose, especially of the inulin and levan types, plants producing α-1,4-glucan, plants producing α-1,6-branched α-1,4-glucan, and plants producing alternans. It is a plant that produces
3) Transgenic plants that produce hyaluronan.
4) Transgenic or hybrid plants, such as onions, with specific properties such as eg "high soluble solids content", "low spiciness" (LP) and/or "long shelf life" (LS).

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be treated according to the invention are plants such as cotton plants that have altered fiber properties. Such plants can be obtained by genetic transformation or selection of plants containing mutations conferring such altered fiber properties, including:
a) Plants such as cotton plants containing modified cellulose synthase genes,
b) a plant such as a cotton plant containing a modified rsw2 or rsw3 homologous nucleic acid, such as a cotton plant with increased expression of sucrose phosphate synthase;
c) plants such as cotton plants with increased expression of sucrose synthase;
d) plants, such as cotton plants, in which the timing of gate opening and closing of plasmodesmata at the base of fiber cells is altered, for example by downregulation of fiber-selective β-1,3-glucanases;
e) Plants such as cotton plants having fibers with altered reactivity, for example by expression of N-acetylglucosamine transferase genes, including nodC, and chitin synthase genes.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be treated according to the invention are plants such as rapeseed or related cruciferous plants that have altered oil profile characteristics. Such plants can be obtained by genetic transformation or by selection of plants containing mutations conferring such altered oil properties, such plants include:
a) Plants such as rapeseed plants that produce oils with high oleic acid content;
b) Plants such as rapeseed that produce oils with low linolenic acid content;
c) Plants such as rapeseed that produce oils with low levels of saturated fatty acids.

Plants or plant cultivars (obtainable by plant biotechnological methods, such as genetic engineering) which can also be treated according to the invention include, for example, potato virus resistant to potato virus Y (Tecnoplant, Argentina). SY230 and SY233 events), or potatoes that are resistant to diseases such as potato blight (e.g., RB gene), or potatoes that exhibit cold-induced reduction in sweetness (those with Nt-Inh, II-INV genes). ) or plants such as potato (A-20 oxidase gene) that exhibit a wilting phenotype.

Plants or plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can also be treated according to the invention are plants such as rapeseed or related cruciferous plants that have altered seed-shedding properties. Such plants can be obtained by genetic transformation or by selection of plants containing mutations conferring such altered characteristics, including plants such as oilseed rape with delayed or reduced seed shedding. It will be done.

Particularly useful transgenic plants that can be treated in accordance with the present invention are the subject of approved or pending applications for non-regulated status in the United States with the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA). A plant having a transformation event or combination of transformation events that is . Information in this regard is always available from APHIS (4700 River Road Riverdale, MD 20737, USA), for example via their website (http://www.aphis.usda.gov/brs/not_reg.html). On the filing date of this application, applications containing the following information were either approved or pending with APHIS:
- Application: Application identification number. A technical description of the transformation event can be found in the specific application document available from APHIS via application number on the website. These descriptions are disclosed herein by reference.
- Extension of application: Reference to previous application for which extension of scope or duration is requested.
- Institution: Name of the person submitting the application.
-Regulated goods: relevant plant species.
- Transgenic phenotype: a trait conferred on a plant by a transformation event.
- Transformation event or lineage: the name of one or more events (often also referred to as one or more lineages) for which an unregulated state is sought.
- APHIS Documents: Various documents issued by APHIS in connection with the application or available from APHIS upon request.

Particularly useful transgenic plants that can be treated according to the invention are those plants that contain one or more genes encoding one or more toxins and are sold under the trade names: Yes: YIELD GARD® (e.g. corn, cotton, soybean), KnockOut® (e.g. corn), BiteGard® (e.g. corn), BT-Xtra® (e.g. corn), StarLink ® (e.g. corn), Bollgard ® (cotton), Nucotn ® (cotton), Nucotn 33B ® (cotton), NatureGard ® (e.g. corn), Protecta ® Trademark) and NewLeaf® (potato). Examples of herbicide tolerant plants are corn varieties, cotton varieties and soybean varieties available under the following trade names: Roundup Ready® (glyphosate tolerant, e.g. corn, cotton, soybean), Liberty Link® Trademark) (resistance to phosphinothricins, e.g. canola), IMI® (resistance to imidazolinones) and SCS® (resistance to sulfonylureas), e.g. corn. Herbicide-tolerant plants (plants grown by conventional methods for herbicide tolerance) that may be mentioned include the varieties sold under the name Clearfield® (eg corn).

Particularly useful transgenic plants that can be treated according to the invention are those that contain a transformation event or a combination of transformation events, such as those listed in the databases of various national or regional regulatory agencies ( For example, see http://gmoinfo.jrc.it/gmp_browse.aspx and http://cera-gmc.org/index.php?evidcode=&hstIDXCode=&gType=&AbbrCode=&atCode=&stCode=&coIDCode=&action=gm_crop_database&mode=Submit ).

The following examples illustrate the invention in more detail.

A. chemistry examples
Preparation of ethyl 3-[5-(2-chlorophenyl)-2-cyclopropylpyrimidin-4-yl]-2-oxopropanoate (Example II-099)
300 mg (1.22 mmol) of 5-(2-chlorophenyl)-2-cyclopropyl-4-methylpyrimidine and 230 mg (1.59 mmol) of diethyl oxalate are dissolved in THF (8 ml) under nitrogen. Subsequently, 1.59 ml of a 1 molar LiHDMS solution (1.59 mmol) is added at a temperature of 0-10°C. After 2 hours at 20° C., the reaction mixture is worked up by extraction with ethyl acetate and water. After separation on silica gel, 63 mg of the desired product are obtained as a yellowish solid.
^1H -NMR (CDCl ₃ , 400MHz): 8.33 (s, 1H), 7.55-7.20 (m, 4H), 6.11 (s, 1H, ), 4.3 (q, 2H) ), 2.23 (m, 1H), 1.35 (t, 3H), 1.30-1.2 (m, 4H).

Preparation of 3-[5-(2-chlorophenyl)-2-cyclopropylpyrimidin-4-yl]-N,N-dimethyl-2-oxopropanamide (Example I-139) in 4 ml of DMF under nitrogen. To the initial charge of 300 mg (1.23 mmol) of 5-(2-chlorophenyl)-2-cyclopropyl-4-methylpyrimidine and 214 mg (1.41 mmol) of ethyl (dimethylamino) (oxo)acetate, 108 mg (2. 70 mmol) of 60% sodium hydride was added. After stirring at room temperature for 12 hours, the reaction was hydrolyzed with 221 mg (3.68 mmol) acetic acid, diluted with water, and extracted with ethyl acetate. After drying the organic phase over sodium sulfate and purification using silica gel, 67 mg of 3-[5-(2-chlorophenyl)-2-cyclopropylpyrimidin-4-yl]-N,N-dimethyl-2-oxo Propanamide was obtained.

Preparation of tert-butyl 2-{3-[5-(2-chlorophenyl)-2-cyclopropylpyrimidin-4-yl]-2-oxopropanoyl}-1-methylhydrazinecarboxylate (Example IV-137)
Initial charge of 362 mg (1.4 mmol) tert-butyl 2-[ethoxy(oxo)acetyl]-1-methylhydrazinecarboxylate and 300 mg (1.2 mmol) 5-(2-chlorophenyl) in 8 ml anhydrous THF. -2-Cyclopropyl-4-methylpyrimidine is cooled to 0° C. under nitrogen and 4.045 ml (4 mmol) of a 1 molar lithium hexamethyldisilazide solution are added. After the reaction has ended, 0.281 ml (4.9 mmol) of glacial acetic acid are added, the mixture is diluted with ethyl acetate and washed with water. After column chromatographic purification, 329 mg of the desired target compound are obtained in solid form.

3-[5-(2-chloro-6-fluorophenyl)-2-cyclopropylpyrimidin-4-yl]-1-(piperidin-1-yl)propane-1,2-dione (Example I-146) Preparation of 80 mg (0.30 mmol) of 5-(2-chloro-6-fluorophenyl)-2-cyclopropyl-4-methylpyrimidine and 75 mg (98%; 0.39 mmol) as in Example IV-137. 45 mg of the desired target compound are obtained as a yellowish oil after column chromatographic purification on silica gel.
^1H -NMR (CDCl ₃ , 400MHz): 8.03 (s, 1H), 7.39-7.08 (m, 3H), 5.3 (s, 1H,), 3.55-3.50 (m, 4H), 2.15-2.08 (m, 1H), 1.67-1.55 (m, 6H), 1.30-1.22 (m, 4H).

Preparation of methyl 3-[2-cyclopropyl-5-(2,6-dichlorophenyl)pyrimidin-4-yl]-2-oxopropanoate (Example II-542)
To 230 mg (0.82 mmol) of 2-cyclopropyl-5-(2,6-dichlorophenyl)-4-methylpyrimidine was added 1.0 ml (0.98 mmol) of lithium hexamethyldisilazide under nitrogen at -78°C. The mixture is warmed to −30° C. and reacted with 149 mg (0.90 mmol) of methyl trimethoxyacetate. After the reaction has ended, hydrolysis is carried out at that temperature with 0.19 ml (3.29 mmol) of glacial acetic acid, the mixture is washed with sodium chloride solution and dried. After column chromatography purification, 150 mg of desired product are obtained with 90% purity.

Preparation of 3-[5-(2-chlorophenyl)-2-cyclopropylpyrimidin-4-yl]-2-oxopropanoic acid (Example II-097) 390 mg (1.17 mmol) in 5 ml THF at 0 °C under nitrogen ) of methyl 3-[5-(2-chlorophenyl)-2-cyclopropylpyrimidin-4-yl]-2-oxopropanoate (prepared similarly to Method II-542) was added with 1.18 ml of 2N hydroxide. Sodium solution was added and the mixture was stirred at room temperature. Acidification with 2N hydrochloric acid and extraction with dichloromethane gives a crude product which can be purified by crystallization to yield 100 mg of the desired target compound.

Preparation of 5-(2-chlorophenyl)-2-cyclopropyl-4-methylpyrimidine (intermediate) An initial charge of 9400 mg (38.7 mmol) of 3-(2-chlorophenyl)- in 40 ml n-butanol under nitrogen. To 4-(dimethylamino)but-3-en-2-one was added 6060 mg (50.3 mmol) of cyclopropanecarboximidamide hydrochloride (1:1) followed by 5.4 mol sodium in methanol. Condensate with 9.307 ml of methoxide solution. The mixture is heated for 7 hours and the volatiles are distilled off. After the reaction has ended, the solvent is removed under reduced pressure and the residue is dissolved in ethyl acetate and washed with water. After drying the organic phase over sodium sulfate, 10.17 mg of an orange liquid are obtained, which is further purified by chromatography on silica gel. 6863 mg of a yellowish oil with a purity of 86% is obtained.
^1H -NMR (CDCl ₃ , 400MHz): 8.3 (s, 1H), 7.51-7.18 (m, 4H), 2.30 (s, 3H), 2.30-2.20 ( m, 1H), 1.2-1.0 (m, 4H).

Preparation of 3-(2-chlorophenyl)-4-(dimethylamino)but-3-en-2-one (intermediate) An initial charge of 5000 mg (29.65 mmol) of 1-(2-chlorophenyl)acetone under nitrogen To this, 5300 mg (44.48 mmol) of 1,1-dimethoxy-N,N-dimethylmethanamine are added and the mixture is heated under reflux for 3 hours, during which time the methanol is distilled off. After the reaction has ended, the mixture is cooled to room temperature, diluted with a 2:1 heptane:ethyl acetate mixture and washed with water. Drying with sodium sulfate gives 7020 mg (95%) of a reddish-brown oil.
^1H -NMR (CDCl ₃ , 400MHz): 7.65 (s, 1H), 7.5-7.15 (m, 4H), 2.73 (bs, 6H), 1.9 (s, 3H) ．．

B. Formulation examples
1. powdered products
A dust product is obtained by mixing 10 parts by weight of the compound of formula (I) with 90 parts by weight of talc as an inert substance and grinding the mixture in a hammer mill.

2. dispersible powder
25 parts by weight of a compound of formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting and dispersing agent. A readily water-dispersible wettable powder is obtained by mixing and grinding the mixture in a pinned disc mill.

3. dispersant
20 parts by weight of the compound of formula (I), 6 parts by weight of alkylphenol polyglycol ether (Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8EO) and 71 parts by weight of paraffinic A readily water-dispersible dispersant is obtained by mixing mineral oil (eg, boiling range above about 255-277°C) and milling the mixture in a friction ball mill to a fineness of less than 5 microns.

Four. emulsion
An emulsion is obtained from 15 parts by weight of a compound of formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.

Five. granule hydrating agent
75 parts by weight of a compound of formula (I),
10 parts by weight of calcium lignosulfonate,
5 parts by weight of sodium lauryl sulfate;
3 parts by weight of polyvinyl alcohol and
Mix 7 parts by weight of kaolin,
Granular wettable powders are obtained by grinding the mixture in a pinned disc mill and granulating the powder in a fluidized bed by spraying water as the granulating liquid.

25 parts by weight of a compound of formula (I),
5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate;
2 parts by weight of sodium oleoylmethyltaurate;
1 part by weight polyvinyl alcohol,
17 parts by weight of calcium carbonate and
It is also possible by homogenizing and pre-milling 50 parts by weight of water in a colloid mill, then milling the mixture in a bead mill and atomizing and drying the suspension thus obtained in a spray tower using a single-phase nozzle. , to obtain a hydrated granule.

C. Biological Examples In the table below, the following abbreviations are used:
ABUTH: Abutilon theophrast AGSTE: Agrostis tenuis
ALOMY: Alopecurus myosuroides
AMARE: Amaranthus retroflexus AVEFA: Oat (Avena fatua)
DIGSA: Digitaria sanguinalis ECHCG: Echinochloa crus-galli
HORMU: Hordeum murinum LOLPE: Lolium perenne
LOLRI: Lolium rigidum MATCH: Chamomile (Matricaria chamonilla)
MATIN: Matricaria inodora POAAN: Poa annua
POLCO: Polygonum convolvulus
SETVI: Setaria viridis STEME: Stellaria media
VERPE: Veronica persica

Test Description Method A: Post-Emergence Herbicidal Activity and Crop Plant Compatibility Seeds of monocotyledonous and dicotyledonous weeds and crop plants are placed in sandy loam soil in plastic or organic pots, covered with soil, and grown under controlled cultivation conditions. , grown in a greenhouse. Two to three weeks after sowing, test plants are treated at the single leaf stage. The compound of the invention, formulated in the form of a wettable powder (WP) or as an emulsion (EC), is then applied at a water application rate (converted) of 600 l/ha with the addition of 0.5% additives. Spray on the green parts of plants as an aqueous suspension or emulsion. After the test plants are maintained in a greenhouse under optimal cultivation conditions for approximately 3 weeks, the activity of the preparation is visually scored in comparison to an untreated control. For example, 100% active = plant died, 0% active = same as control plant.

The results show that the compounds of the present invention, such as compound numbers II-099, I-139, I-137, II-098 and other compounds in Table A, are effective against harmful plants when applied post-emergence. Has very good weeding effect. For example, compound no. It has very good herbicidal activity (80% to 100% herbicidal activity) on plants. At the same time, some compounds of the invention cause little damage to grass crops such as barley, wheat, rye, millet/sorghum, maize, rice or sugarcane when applied post-emergence, even at high active compound application rates. I won't give it. Additionally, some substances are also harmless to dicotyledonous crops such as soybean, cotton, rapeseed or sugar beet.

Some of the compounds of the invention have high selectivity and are therefore suitable for controlling unwanted vegetation in agricultural crops by post-emergence methods.

Method B: Pre-emergent herbicidal action and crop plant compatibility Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are placed in plastic or organic pots and covered with soil. The compound of the invention, formulated in the form of a wettable powder (WP) or as an emulsion (EC), is then applied at a water application rate (converted) of 600 l/ha with the addition of 0.5% additives. Apply as an aqueous suspension or emulsion onto the surface of the covered soil. After treatment, the pots are placed in a greenhouse and kept under good cultivation conditions for test plants. After approximately 3 weeks, the efficacy of the formulation is visually scored as a percentage compared to the untreated control. For example, 100% active = plant died, 0% active = same as control plant.

The results show that the compounds of the invention, such as compound numbers II-099, I-139, I-137 and II-098 of Table B, and other compounds, are effective against harmful plants when applied pre-emergent. It has a very good herbicidal effect. For example, compounds Nos. II-099 and I-139, when applied pre-emergence, can be applied to grasshoppers, staghorn, oats, goldenrod, wheatgrass, bowweed, buckwheat and chickweed at application rates of up to 0.32 kg of active substance per hectare. It has very good herbicidal activity (80% to 100% herbicidal activity) against harmful plants such as. At the same time, some of the compounds of the invention, even at high active compound doses, when applied pre-emergence, substantially destroy grass crops such as barley, wheat, rye, millet/sorghum, maize, rice or sugarcane. Leave undamaged. Additionally, some substances are also harmless to dicotyledonous crops such as soybean, cotton, rapeseed or sugar beet.

Some of the compounds of the invention exhibit high selectivity and are therefore suitable for controlling unwanted vegetation in agricultural crops by pre-emergence methods.

Method C: Post-emergence action of herbicides Seeds of monocot and dicot weed plants are placed in sandy loam soil in plastic pots (double one seed of each monocot or dicot weed plant per pot). (sown), covered with soil and grown in a greenhouse under controlled growing conditions. Two to three weeks after sowing, test plants are treated at the single leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsions (EC), are then aqueous with the addition of 0.5% additives at a water application rate equal to 600 l/ha. Apply as a suspension or emulsion to the green parts of the plant. After the test plants are maintained in a greenhouse under optimal cultivation conditions for approximately 3 weeks, the activity of the preparation is visually scored in comparison to an untreated control. For example, 100% active = plant died, 0% active = same as control plant.

The results show that the compounds of the present invention, such as compound numbers I-137, IV-137 and II-098 in Table C, and other compounds, have very good performance against harmful plants when applied post-emergence. Has a weeding effect. For example, at an application rate of up to 1.28 kg of active substance per hectare, compound No. I-137 can be used on Echinochloa crus-galli, horseweed (Lolium rigidum), dogweed (Matricaria inodora) when applied post-emergence. Compound II-098 has very good herbicidal activity (80% to 100% herbicidal activity) against harmful plants such as Poa annua, and Stellaria media. In some cases, very good herbicidal activity (80% to 100% herbicidal action).

Method D: Pre-emergence action of herbicides Seeds of monocot and dicot weed plants are placed in sandy loam soil in plastic pots (one seed of each monocot or dicot weed plant is doubled per pot). sow) and cover with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsions (EC), are then added to a water application rate of 600 liters/ha (equivalent) with the addition of 0.5% additives. applied as an aqueous suspension or emulsion onto the surface of the soil it covers. After treatment, the pots are placed in a greenhouse and kept under good cultivation conditions for test plants. After approximately 3 weeks, the efficacy of the formulation is visually scored as a percentage compared to the untreated control. For example, 100% active = plant died, 0% active = same as control plant.

The results show that the compounds of the invention, such as compound numbers IV-137, I-137 and II-098 in Table D, and other compounds, are very effective against harmful plants when applied pre-emergent. It has a strong weeding effect. For example, compounds Nos. I-137 and IV-137, when applied pre-emergence, can be applied to grasshoppers, goldenrod (Echinochloa crus-galli), barley (Lolium rigidum), at application rates of up to 1.28 kg of active substance per hectare. It has very good herbicidal activity (80% to 100% herbicidal activity) against harmful plants such as Poa annua and Stellaria media.

Method E: Early Post-Emergence Action of Herbicides Seeds of monocotyledonous or dicotyledonous weed plants were placed in silica sand in 96-well microtiter plates and grown in an acclimatized chamber under controlled cultivation conditions. . 5-7 days after sowing, test plants are treated at the cotyledon stage. The compounds of the invention formulated in the form of an emulsion (EC) are applied at a water application rate equivalent to 2200 liters/ha. After placing the test plants in an acclimatization chamber for 9-12 days under optimal cultivation conditions, the efficacy of the preparation is visually scored in comparison to the untreated control. For example, 100% active = plant died, 0% active = same as control plant.

The results show that the compounds of the invention, such as compound numbers I-147, I-547, II-099 or IV-137 of Table E, and other compounds, when applied early after emergence, are effective against harmful plants. It has a very good herbicidal effect against. For example, with an application rate of up to 1900 g of active substance per hectare, compound number I-147, I-547 or IV-137 can be applied to Agrostis tenuis, Lolium perenne, when applied post-emergence. Compound II-099 and I-688 has very good herbicidal activity (80% to 100%) against harmful plants such as Agrostis tenuis, Matricaria chamonilla and Poa annua when applied post-emergence. herbicidal action).

Claims (11)

Compound of general formula (I)
(wherein the symbols and exponents have the following meanings:
X represents C(R ¹³ )(R ¹⁴ )
R ¹ represents (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl or heterocyclyl, where these three above groups are respectively halogen, (C ₁ -C ₆ ) -Alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, halo-(C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, halo -(C ₃ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, halo-(C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, halo-(C ₃ - _C6 )-cycloalkenyl, ( _C3 - _C6 )-cycloalkyl-( _C1 - _{C6)-alkyl, (C3-C6 ) -cycloalkenyl-} ( _C1 - _C6 )-alkyl , halo-(C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, halo-(C ₃ -C ₆ )-cycloalkenyl-(C ₁ -C ₆ )-alkyl, R ⁸ ( O)C, ^R8O (O)C, ( ^R8 ) _2N (O)C, ^R8O , ( ^R8 ) _2N , ^R9 (O) _nS , phenyl, heteroaryl, heterocyclyl, phenyl substituted by s groups of the group consisting of -(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl and heterocyclyl-(C ₁ -C ₆ )-alkyl, where and these phenyl, heteroaryl, heterocyclyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl and heterocyclyl-(C ₁ -C ₆ )-alkyl are ( m members of the group consisting of C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkoxy, halo-(C ₁ -C ₆ )-alkoxy, and halogen. wherein cycloalkyl, cycloalkenyl and heterocyclyl each independently have n oxo groups;
R ² is hydroxy, (C ₁ -C ₆ )-alkoxy, (C ₂ -C ₆ )-alkenyloxy, (C ₂ -C ₆ )-alkynyloxy, (C ₁ -C ₆ )-haloalkoxy, ( C ₂ -C ₆ )-haloalkenyloxy, (C ₂ -C ₆ )-haloalkynyloxy, where these (C ₁ -C ₆ )-alkoxy, (C ₂ -C ₆ )-alkenyloxy , (C ₂ -C ₆ )-alkynyloxy, (C ₁ -C ₆ )-haloalkoxy, (C ₂ -C ₆ )-haloalkenyloxy, and (C ₂ -C ₆ )-haloalkynyloxy , respectively, Cyano, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, halo-(C ₃ -C ₆ )-cycloalkyl, halo-(C ₃ -C ₆ )-cycloalkenyl, R ⁸ (O)C, R ⁸ (R ⁸ ON=)C, R ⁸ O(O)C, R ⁹ S(O)C, (R ⁸ ) ₂ N(O)C, R ⁸ (R ⁸ O )N(O)C, ( ^R8 ) ₂ N( ^R8 )N(O)C, ^R8 (O)C( ^R8 )N(O)C, ^R9 O(O)C( ^R8 ) N(O)C, (R ⁸ ) ₂ N(O)C(R ⁸ )N(O)C, R ⁹ (O) ₂ S(R ⁸ )N(O)C, R ⁸ O(O) ₂ S( ^R8 )N(O)C, ( ^R8 ) _2N (O) _2S ( ^R8 )N(O)C, ^R8O , ^R8 (O)CO, ^R9 (O) _2SO , R ⁹ O (O) CO, (R ⁸ ) ₂ N (O) CO, (R ⁸ ) ₂ N, R ⁸ (O) C (R 8 ) N, R ⁹ ( ^O ) ₂ S (R ⁸ ) N, R ⁹ O(O)C(R ⁸ )N, (R ⁸ ) ₂ N(O)C(R ⁸ )N, R ⁸ O(O) ₂ S(R ⁸ )N, (R ⁸ ) ₂ N(O) ₂ S(R ⁸ ) N, R ⁹ (O) _n S, R ⁸ O(O) ₂ S, (R ⁸ ) ₂ N(O) ₂ S, R ⁸ (O) C(R ⁸ )N(O) ₂ S, R ⁹ O(O)C(R ⁸ )N(O) ₂ S, (R ⁸ ) ₂ N(O)C(R ⁸ )N(O) ₂ S, R ¹¹ ₃ substituted by s groups of the group consisting of Si, (R ¹² O) ₂ (O)P, phenyl, heteroaryl and heterocyclyl, where phenyl, heteroaryl and heterocyclyl are each nitro, Halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl, or
or
R ² represents (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-cycloalkenyloxy, phenyloxy, heteroaryloxy or heterocyclyloxy, and these five above groups each represent halogen , cyano, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C _{6 )} - )-cycloalkenyl, halo-(C ₃ -C ₆ )-cycloalkyl, halo-(C ₃ -C ₆ )-cycloalkenyl, R ⁸ (O)C, R ⁸ (R ⁸ ON=)C, R ⁸ O(O)C, R ⁹ S(O)C, (R ⁸ ) ₂ N(O)C, R ⁸ (R ⁸ O) N(O)C, (R ⁸ ) ₂ N(R ⁸ ) N( O)C, ^R8 (O)C( ^R8 ) N(O)C, ^R9 O(O)C( ^R8 ) N(O)C, ( ^R8 ) ₂ N(O)C( ^R8 )N(O)C, ^R9 (O) _2S ( ^R8 )N(O)C _, R8O(O) _2S ( ^R8 )N(O)C, ( ^R8 ) ^2N (O ⁾ ₂ S( ^R8 )N(O)C _, ^R8O , R8(O)CO, ^R9 (O)2SO, ^R9O (O)CO, ( ^R8 ) _2N (O)CO , ( ^R8 ) _2N , ^R8 (O)C( ^R8 )N, ^R9 (O) _2S (R8)N, ^R9O ( ^O )C( ^R8 )N, ( ^R8 ) ₂ N(O)C(R ⁸ )N, R ⁸ O(O) ₂ S(R ⁸ )N, (R ⁸ ) ₂ N(O) ₂ S(R ⁸ )N, R ⁹ (O) _n S , ^R8O (O) _2S , ( ^R8 )2N(O) _2S , _R8 (O)C( ^R8 )N(O) _2S , ^R9O ( ^O )C( ^R8 ) N(O ⁾ _2S , ( ^R8 ) _2N (O)C( ^R8 )N(O) _2S , _R311Si , ( ^R12O ) ₂ (O)P, phenyl, heteroaryl and heterocyclyl s groups of the group consisting of phenyl, heteroaryl and heterocyclyl , respectively, nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-( C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ to C ₆ )-alkyl, where (C ₃ -C ₆ )-cycloalkyl, (C 3 -C 6 )-cycloalkenyl, heterocyclyl, (C ₃ -C ₆ )-cycloalkyl, (C 3 -C 6 )-cycloalkenyl, (C ₃ -C ₆ )-cycloalkenyl, -cycloalkoxy, (C ₃ -C ₆ )-cycloalkenyloxy and heterocyclyloxy each independently have n oxo groups, or
R ² represents R ⁸ (O) CO, R ⁹ (O) ₂ SO or R ¹⁵ R ¹⁶ C=N−O or (R ⁸ ) ₂ N−O, or
or
R ² is (R ⁸ ) ₂ N, R ⁸ (O) C (R ⁸ ) N, R ⁹ O (O) C (R ⁸ ) N, (R ⁸ ) ₂ N (O) C (R ⁸ ) N, ^R9 (O) _2S ( ^R8 )N, ^R8O (O) _2S ( ^R8 )N, or ( ^R8 ) _2N (O) _2S ( ^R8 )N,
or
R ² represents R ⁸ (R ⁸ O)N or
R ² represents (R ¹⁷ )(R ¹⁸ )N(R ¹⁹ )N, or
or
R ² represents R ¹⁷ R ¹⁸ C=N-(R ¹⁹ )N-,
R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen, nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )- Alkyl, (C ₂ -C ₆ )-alkenyl, halo-(C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, halo-(C ₃ -C ₆ )-alkynyl, (C ₃ - C ₆ )-cycloalkyl, halo-(C ₃ to C ₆ )-cycloalkyl, (C ₃ to C ₆ )-cycloalkyl-(C ₁ to C ₆ )-alkyl, halo-(C ₃ to C ₆ ) -Cycloalkyl-(C ₁ to C ₆ )-alkyl, R ⁸ (O)C, R ⁸ (R ⁸ ON=)C, R ⁸ O(O)C, (R ⁸ ) ₂ N(O)C, ^R8 ( ^R8O )N(O)C, ( ^R8 ) _2N ( ^R8 )N ^{(O)C, R8(O)C(R8 )} N(O)C, ^R9O (O )C( ^R8 )N(O)C,( ^R8 ) _2N (O)C( ^R8 )N(O)C, ^R9 (O) _2S ( ^R8 )N(O)C,R ⁸ O(O) ₂ S(R ⁸ )N(O)C, (R ⁸ ) ₂ N(O) ₂ S(R ⁸ )N(O)C, R ⁸ O, R ⁸ (O)CO, R ⁹ (O) ₂ SO, R ⁹ O (O) CO, (R ⁸ ) ₂ N (O) CO, (R ⁸ ) ₂ N, R ⁸ (O) C (R ⁸ ) N, R ⁹ (O) ₂ S(R ⁸ )N, R ⁹ O(O)C(R ⁸ )N, (R ⁸ ) ₂ N(O)C(R ⁸ )N, R ⁸ O(O) ₂ S(R ⁸ )N , (R ⁸ ) ₂ N(O) ₂ S(R ⁸ )N, R ⁹ (O) _n S, R ⁸ O(O) ₂ S, (R ⁸ ) ₂ N(O) ₂ S, R ⁸ ( O)C( ^R8 )N(O) _2S , ^R9O (O)C( ^R8 )N(O) _2S ,( ^R8 ) _2N (O)C( ^R8 )N(O) ₂ S, (R ¹² O) ₂ (O)P, R ⁸ (O)C-(C ₁ -C ₆ )-alkyl, R ⁸ O(O)C-(C ₁ -C ₆ )-alkyl, ( R ⁸ ) ₂ N(O)C-(C ₁ to C ₆ )-alkyl, (R ⁸ O)(R ⁸ )N(O)C-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(R ⁸ )N(O)C-(C ₁ to C ₆ )-alkyl, R ⁸ (O)C(R ⁸ )N(O)C-(C ₁ to C ₆ )-alkyl, R ⁹ O (O)C(R ⁸ )N(O)C-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O)C(R ⁸ )N(O)C-(C ₁ to C ₆ )-alkyl, R ⁹ (O) ₂ S(R ⁸ )N(O)C-(C ₁ ~C ₆ )-alkyl, R ⁸ O(O) ₂ S(R ⁸ )N(O)C-( C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O) ₂ S(R ⁸ )N(O)C-(C ₁ to C ₆ )-alkyl, NC-(C ₁ to C ₆ )- Alkyl, R ⁸ O-(C ₁ -C ₆ )-alkyl, R ⁸ (O)CO-(C ₁ -C ₆ )-alkyl, R ⁹ (O) ₂ SO-(C ₁ -C ₆ )-alkyl , R ⁹ O(O)CO-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O)CO-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N-(C ₁ ~C ₆ )-alkyl, R ⁸ (O)C(R ⁸ )N-(C ₁ to C ₆ )-alkyl, R ⁹ (O) ₂ S(R ⁸ )N-(C ₁ to C ₆ )- Alkyl, R ⁹ O(O)C(R ⁸ )N-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O)C(R ⁸ )N-(C ₁ to C ₆ )-alkyl , R ⁸ O(O) ₂ S(R ⁸ )N-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O) ₂ S(R ⁸ )N-(C ₁ to C ₆ )- Alkyl, R ⁹ (O) _n S-(C ₁ to C ₆ )-alkyl, R ⁸ O(O) ₂ S-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O) ₂ S -(C ₁ to C ₆ )-alkyl, R ⁸ (O)C(R ⁸ )N(O) ₂ S-(C ₁ to C ₆ )-alkyl, R ⁹ O(O)C(R ⁸ )N (O) ₂ S-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O)C(R ⁸ )N(O) ₂ S-(C ₁ to C ₆ )-alkyl, (R ¹² O) ₂ (O)P-(C ₁ -C ₆ )-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl or Heterocyclyl-(C ₁ -C ₆ )-alkyl, where these phenyl, heteroaryl, heterocyclyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl or heterocyclyl-(C ₁ -C ₆ )-alkyl is nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C _{3 -C} 6 )-alkyl, respectively. ₆ )-Cycloalkyl, R ⁸ O(O)C, (R ⁸ ) ₂ N(O)C, R ⁸ O, (R ⁸ ) ₂ N, R ⁹ (O) _n S, R ⁸ O(O) ₂ S, (R ⁸ ) ₂ N(O) ₂ S and R ⁸ O-(C ₁ -C ₆ )-alkyl, where cycloalkyl and heterocyclyl are Each independently has n oxo groups,
R ⁸ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkenyl-(C ₁ -C ₆ )-alkyl, (C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, (C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkenyl- (C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl or (C ₁ -C ₆ )-alkylthio-(C ₁ -C ₆ )-alkyl, where these ( C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl , (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkenyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )- -Alkyl-O-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl, ( C ₃ to C ₆ )-cycloalkyl-(C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, (C ₃ to C ₆ )-cycloalkenyl-(C ₁ to C ₆ ) -Alkyl-O-(C ₁ -C ₆ )-alkyl or (C ₁ -C ₆ )-alkylthio-(C ₁ -C ₆ )-alkyl has s halogen atoms,
or
R ⁸ is phenyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl- O-(C ₁ -C ₆ )-alkyl, heteroaryl-O-(C ₁ -C ₆ )-alkyl, heterocyclyl-O-(C ₁ -C ₆ )-alkyl, phenyl-N(R ¹⁰ )-( _C1 - _C6 )-alkyl, heteroaryl-N( ^R10 )-(C1 _{- C6} )-alkyl, heterocyclyl-N( ^R10 )-( _C1 - _C6 )-alkyl, phenyl-S( O) _n -(C ₁ -C ₆ )-alkyl, heteroaryl-S(O) _n -(C ₁ -C ₆ )-alkyl or heterocyclyl-S(O) _n -(C ₁ -C ₆ )-alkyl , where these groups are nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ ), respectively. -Cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n substituted by m groups of the group consisting of S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl; ,
and (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl and heterocyclyl each independently have n oxo groups,
or
The R ⁸ groups are combined with one or more heteroatoms to which they are attached: heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl , where each of these rings in turn is nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ ~C ₆ )-alkyl, (C ₃ ~C ₆ )-cycloalkyl, (C ₃ ~C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O－(C ₁ to C ₆ )－ substituted by m groups of the group consisting of alkyl and oxo,
R ⁹ is (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-Cycloalkenyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkenyl-(C ₁ -C ₆ )-alkyl, (C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, (C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkenyl-(C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl or (C ₁ -C ₆ )-alkylthio-(C ₁ -C ₆ )-alkyl, where these groups are has s halogen atoms, or
or
R ⁹ is phenyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl- O-(C ₁ -C ₆ )-alkyl, heteroaryl-O-(C ₁ -C ₆ )-alkyl, heterocyclyl-O-(C ₁ -C ₆ )-alkyl, phenyl-N(R ¹⁰ )-( _C1 - _C6 )-alkyl, heteroaryl-N( ^R10 )-(C1 _{- C6} )-alkyl, heterocyclyl-N( ^R10 )-( _C1 - _C6 )-alkyl, phenyl-S( O) _n -(C ₁ -C ₆ )-alkyl, heteroaryl-S(O) _n -(C ₁ -C ₆ )-alkyl or heterocyclyl-S(O) _n -(C ₁ -C ₆ )-alkyl , where these groups are nitro, halogen, cyano, thiocyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ ), respectively. -Cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n substituted by m groups of the group consisting of S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl; ,
and (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl and heterocyclyl each independently have n oxo groups,
R ¹⁰ is hydrogen, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ - _C6 )-cycloalkyl, ( _C3 - _C6 )-cycloalkyl-( _C1 - _C6 )-alkyl or phenyl;
R ¹¹ is (C ₁ to C ₆ )-alkyl, halo-(C ₁ to C ₆ )-alkyl, (C ₂ to C ₆ )-alkenyl, (C ₂ to C ₆ )-alkynyl, (C ₃ to C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl or phenyl,
R ¹² represents hydrogen or (C ₁ -C ₄ )-alkyl;
R ¹³ and R ¹⁴ are each independently hydrogen, (C ₁ -C ₆ )-alkyl, hydroxy, (C ₁ -C ₆ )-alkoxy, (R ⁸ ) ₂ N, halo-(C ₁ -C ₆ )-alkoxy, halogen, halo-(C ₁ -C ₆ )-alkyl, cyano, R ⁸ O(O)C or (R ⁸ ) ₂ N(O)C,
or
R ¹³ and R ¹⁴ together with the carbon atom to which they are attached form a (C ₃ -C ₈ )-cycloalkyl group;
R ¹⁵ and R ¹⁶ each independently represent (C ₁ -C ₆ )-alkyl, phenyl, (C ₃ -C ₆ )-cycloalkyl, heteroaryl or heterocyclyl;
R ¹⁷ and R ¹⁸ and R ¹⁹ are independently R ⁸ or R ⁹ S(O) ₂ , (R ⁸ ) ₂ NS(O) ₂ , R ⁸ OS(O) ₂ , R ⁹ C(O), (R ⁸ ) ₂ NC(O), (R ⁸ ) ₂ NC(S), R ⁸ OC(O), R ⁸ OC(O) C(O), (R ⁸ ) ₂ NC(O) C(O ) or
or
(R ¹⁷ and R ¹⁸ ) or (R ¹⁷ and R ¹⁹ ) groups with one or more heteroatoms to which they are attached: heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, forming a ring selected from heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn is nitro, halogen, cyano, thiocyano, (C ₁ to C ₆ )-alkyl, halo-(C ₁ to C ₆ )-alkyl, (C ₃ to C ₆ )-cycloalkyl, (C ₃ to C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl and oxo,
m represents 0, 1, 2, 3, 4 or 5;
n represents 0, 1 or 2;
s represents 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11)
and its agriculturally acceptable salts. A compound of formula (I) according to claim 1, comprising:
X represents C(R ¹³ )(R ¹⁴ ),
R ¹ represents (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl or heterocyclyl, where these three groups are respectively halogen, (C _{1 -C 6 )-cycloalkyl, (C 3} -C ₆ )-cycloalkenyl or heterocyclyl; )-alkyl and halo-(C ₁ -C ₆ )-alkyl, where cycloalkyl, cycloalkenyl and heterocyclyl each independently have n oxo groups. ,
R ² is hydroxy, (C ₁ -C ₆ )-alkoxy, (C ₂ -C ₆ )-alkenyloxy, (C ₂ -C ₆ )-alkynyloxy, (C ₁ -C ₆ )-haloalkoxy, ( C ₂ -C ₆ )-haloalkenyloxy, (C ₂ -C ₆ )-haloalkynyloxy, where these (C ₁ -C ₆ )-alkoxy, (C ₂ -C ₆ )-alkenyloxy , (C ₂ -C ₆ )-alkynyloxy, (C ₁ -C ₆ )-haloalkoxy, (C ₂ -C ₆ )-haloalkenyloxy, (C ₂ -C ₆ )-haloalkynyloxy is cyano, ^R8 (O)C, ^R8O (O)C, ( ^R8 ) _2N (O)C, ^R8 ( ^R8O )N(O)C, ( ^R8 ) _2N ( ^R8 )N s of the group consisting of (O)C, ^R8O , ^R8 (O)CO, ^R9 (O) _2SO , ( ^R8 ) _2N , ^R9 (O) _nS , phenyl, heteroaryl and heterocyclyl where phenyl, heteroaryl and heterocyclyl are each substituted with nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )- Alkyl, (C ₃ -C ₆ )-cycloalkyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S , R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl, where (C ₃ -C ₆ )-cycloalkyl and heterocyclyl each independently have n oxo groups, or
or
R ² represents (C ₃ -C ₆ )-cycloalkoxy, (C ₃ -C ₆ )-cycloalkenyloxy, phenyloxy, heteroaryloxy or heterocyclyloxy, in which each of these five above-mentioned groups , halogen, cyano, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ - C ₆ )-cycloalkenyl, halo-(C ₃ -C ₆ )-cycloalkyl, halo-(C ₃ -C ₆ )-cycloalkenyl, R ⁸ (O)C, R ⁸ O(O)C, (R ⁸ ) ₂ N(O)C, ^R8 ( ^R8O )N(O)C, (R8) _2N ( ^R8 )N(O)C, ^R8O , ^{R8 (} O)CO, R ⁹ (O) ₂ SO, (R ⁸ ) ₂ N, R ⁹ (O) _n S, phenyl, heteroaryl and heterocyclyl, substituted by s groups,
Here, these phenyl, heteroaryl and heterocyclyl are nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ ), respectively. -Cycloalkyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S , (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl, where (C ₃ -C ₆ )- Cycloalkoxy, (C ₃ -C ₆ )-cycloalkyl and heterocyclyl each independently have n oxo groups,
or
R ² is (R ⁸ ) ₂ N, R ⁸ (O) C (R ⁸ ) N, R ⁹ O (O) C (R ⁸ ) N, (R ⁸ ) ₂ N (O) C (R ⁸ ) N, R ⁹ (O) ₂ S (R ⁸ ) N, R ⁸ O (O) ₂ S (R ⁸ ) N, (R ⁸ ) ₂ N (O) ₂ S (R ⁸ ) N,
or
Does R ² represent R ⁸ (R ⁸ O)N or
whether R ² represents (R ¹⁷ )(R ¹⁸ )N(R ¹⁹ )N;
or
R ² represents R ¹⁷ R ¹⁸ C=N−(R ¹⁹ )N−,
R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen, nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl, (C ₂ -C ₆ )-alkynyl, (C ₃ -C ₆ )-cycloalkyl, halo-(C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkyl )-cycloalkyl-(C ₁ -C ₆ )-alkyl, halo-(C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, R ⁸ (O)C, R ⁸ (R ⁸ ON=)C, R ⁸ O(O)C, (R ⁸ ) ₂ N(O)C, R ⁸ O, (R ⁸ ) ₂ N, R ⁸ (O)C(R ⁸ )N, R ⁹ ( O) ₂ S (R ⁸ ) N, R ⁹ O (O) C (R ⁸ ) N, (R ⁸ ) ₂ N (O) C (R ⁸ ) N, R ⁹ (O) _n S, R ⁸ O (O) ₂ S, (R ⁸ ) ₂ N(O) ₂ S, (R ¹² O) ₂ (O) P, R ⁸ (O) C-(C ₁ to C ₆ )-alkyl, R ⁸ O( O) C-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O)C-(C ₁ to C ₆ )-alkyl, NC-(C ₁ to C ₆ )-alkyl, R ⁸ O -(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N-(C ₁ to C ₆ )-alkyl, R ⁸ (O)C(R ⁸ )N-(C ₁ to C ₆ )-alkyl, R ⁹ (O) ₂ S(R ⁸ )N-(C ₁ to C ₆ )-alkyl, R ⁹ O(O)C(R ⁸ )N-(C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O)C(R ⁸ )N-(C ₁ to C ₆ )-alkyl, R ⁹ (O) _n S-(C ₁ to C ₆ )-alkyl, R ⁸ O(O) ₂ S-( C ₁ to C ₆ )-alkyl, (R ⁸ ) ₂ N(O) ₂ S-(C ₁ to C ₆ )-alkyl, (R ¹² O) ₂ (O)P-(C ₁ to C ₆ )- represents alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, where , these phenyl, heteroaryl, heterocyclyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl, and heterocyclyl-(C ₁ -C ₆ )-alkyl are, respectively, Nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, R ⁸ O, (R ⁸ ) ₂ N, R ⁹ (O) _n S, R ⁸ O substituted by m groups of the group consisting of (O) ₂ S, (R ⁸ ) ₂ N(O) ₂ S and R ⁸ O-(C ₁ -C ₆ )-alkyl, where heterocyclyl is n has oxo groups,
R ⁸ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-( C ₁ to C ₆ )-alkyl, (C ₃ to C ₆ )-cycloalkyl-(C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, phenyl, phenyl-(C ₁ to C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl-O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl, where phenyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl-O-( C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl is nitro, halogen, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-, respectively. Alkyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S and R ¹⁰ O−(C ₁ to C ₆ )-alkyl, where the heterocyclyl has n oxo groups, or
or wherein said two R ⁸ groups have one or more heteroatoms to which they are attached, and , heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn represents halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ ~C ₆ )-alkyl, (C ₃ ~C ₆ )-cycloalkyl, (C ₃ ~C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O－(C ₁ to C ₆ )－ substituted by m groups of the group consisting of alkyl and oxo,
R ⁹ is (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-(C ₁ ~C ₆ )-Alkyl, (C ₃ ~C ₆ )-Cycloalkyl-(C ₁ ~C ₆ )-Alkyl-O-(C ₁ ~C ₆ )-Alkyl, Phenyl, Phenyl-(C ₁ ~C _{6 )} )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl -O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl, where these phenyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl , heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl-O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl is respectively nitro, halogen, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl substituted with m groups of the group consisting of, where the heterocyclyl has n oxo groups,
R ¹⁰ represents hydrogen or (C ₁ -C ₆ )-alkyl,
R ¹¹ represents (C ₁ -C ₆ )-alkyl,
R ¹² represents (C ₁ -C ₄ )-alkyl,
R ¹³ and R ¹⁴ are each independently hydrogen, (C ₁ -C ₆ )-alkyl, hydroxy, (C ₁ -C ₆ )-alkoxy, (R ⁸ ) ₂ N, halo-(C ₁ -C ₆ )-alkoxy, halogen, halo-(C ₁ -C ₆ )-alkyl, cyano, R ⁸ O(O)C or (R ⁸ ) ₂ N(O)C,
or
R ¹³ and R ¹⁴ together with the carbon atom to which they are attached form a (C ₃ -C ₈ )-cycloalkyl group;
R ¹⁵ and R ¹⁶ each independently represent (C ₁ -C ₆ )-alkyl, phenyl, (C ₃ -C ₆ )-cycloalkyl, heteroaryl or heterocyclyl;
R ¹⁷ , R ¹⁸ and R ¹⁹ are independently R ⁸ or R ⁹ S(O) ₂ , (R ⁸ ) ₂ NS(O) ₂ , R ⁸ OS(O) ₂ , R ⁹ C(O), (R ⁸ ) ₂ NC(O), (R ⁸ ) ₂ NC(S), R ⁸ OC(O), R ⁸ OC(O) C(O), (R ⁸ ) ₂ NC(O) C(O ), or the (R ¹⁷ and R ¹⁸ ) or (R ¹⁷ and R ¹⁹ ) groups are combined with one or more heteroatoms to which they are attached: heterocyclyl, heterocyclenyl, heteroaryl, aryl forming a ring selected from heterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn represents halogen, cyano , (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O )C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O ) ₂ S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl and oxo,
m represents 0, 1, 2, 3, 4 or 5,
n represents 0, 1 or 2,
2. A compound of formula (I) according to claim 1, wherein s represents 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11. A compound of formula (I) according to claim 1 or 2, comprising:
X represents C(R ¹³ )(R ¹⁴ ),
R ¹ represents (C ₃ -C ₆ )-cycloalkyl, where the cycloalkyl group is selected from halogen, (C ₁ -C ₆ )-alkyl and halo-(C ₁ -C ₆ )-alkyl. substituted by s groups of the group
R ² is hydroxy, (C ₁ -C ₆ )-alkoxy, (C ₁ -C ₆ )-haloalkoxy, (C ₂ -C ₆ )-alkenyloxy, (C ₂ -C ₆ )-haloalkenyloxy, (C ₂ -C ₆ )-alkynyloxy, where these (C ₁ -C ₆ )-alkoxy, (C ₁ -C ₆ )-haloalkoxy, (C ₂ -C ₆ )-alkenyloxy, (C ₂ -C ₆ )-haloalkenyloxy and (C ₂ -C ₆ )-alkynyloxy are R ⁸ (O)C, R ⁸ O(O)C, and (R ⁸ ) ₂ N(O), respectively. C, R ⁸ (R ⁸ O)N(O)C, (R ⁸ ) ₂ N(R ⁸ )N(O)C, R ⁸ O and phenyl, where this Phenyl is defined by m radicals of the group consisting of nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl and (C ₃ -C ₆ )-cycloalkyl. has been replaced or
or
R ² is (R ⁸ ) ₂ N, R ⁸ (O) C (R ⁸ ) N, R ⁹ O (O) C (R ⁸ ) N, (R ⁸ ) ₂ N (O) C (R ⁸ ) N, R ⁹ (O) ₂ S (R ⁸ ) N, R ⁸ O (O) ₂ S (R ⁸ ) N, (R ⁸ ) ₂ N (O) ₂ S (R ⁸ ) N,
or
Does R ² represent R ⁸ (R ⁸ O)N or
whether R ² represents (R ¹⁷ )(R ¹⁸ )N(R ¹⁹ )N;
or
R ² represents R ¹⁷ R ¹⁸ C=N-(R ¹⁹ )N-
R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen, nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, R ⁸ O(O)C, R ⁸ O or R ⁹ (O) _n S;
R ⁸ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-( C ₁ to C ₆ )-alkyl, (C ₃ to C ₆ )-cycloalkyl-(C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, phenyl, phenyl-(C ₁ to C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, represents heteroaryl-O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl, where phenyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl-O-( C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl is respectively nitro, halogen, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl , R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S and R ¹⁰ O−(C ₁ to C ₆ ) - substituted by m groups of the group consisting of alkyl, where the heterocyclyl has n oxo groups,
or
two R ⁸ groups with one or more heteroatoms to which they are attached: heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclyl forming a ring selected from heteroaryl or heterocyclenylheteroaryl, where each of these rings in turn represents nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ ~C ₆ )-alkyl, (C ₃ ~C ₆ )-cycloalkyl, (C ₃ ~C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O－(C ₁ to C ₆ )－ substituted by m groups of the group consisting of alkyl and oxo,
R ⁹ is (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-(C ₁ ~C ₆ )-Alkyl, (C ₃ ~C ₆ )-Cycloalkyl-(C ₁ ~C ₆ )-Alkyl-O-(C ₁ ~C ₆ )-Alkyl, Phenyl, Phenyl-(C ₁ ~C _{6 )} )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl -O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl, where these phenyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl , heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl-O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl is respectively nitro, halogen, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl substituted with m groups of the group consisting of, where the heterocyclyl has n oxo groups,
R ¹⁰ represents hydrogen or (C ₁ -C ₆ )-alkyl,
R ¹¹ represents (C ₁ -C ₆ )-alkyl,
R ¹² represents (C ₁ -C ₄ )-alkyl,
R ¹³ and R ¹⁴ each independently represent hydrogen, (C ₁ -C ₆ )-alkyl, cyano, R ⁸ O(O)C or (R ⁸ ) ₂ N(O)C,
R ¹⁵ and R ¹⁶ each independently represent (C ₁ -C ₆ )-alkyl, phenyl, (C ₃ -C ₆ )-cycloalkyl, heteroaryl or heterocyclyl;
R ¹⁷ , R ¹⁸ and R ¹⁹ are independently R ⁸ or R ⁹ S(O) ₂ , (R ⁸ ) ₂ NS(O) ₂ , R ⁸ OS(O) ₂ , R ⁹ C(O), (R ⁸ ) ₂ NC(O), (R ⁸ ) ₂ NC(S), R ⁸ OC(O), R ⁸ OC(O) C(O), (R ⁸ ) ₂ NC(O) C(O ) or
or (R ¹⁷ and R ¹⁸ ) or (R ¹⁷ and R ¹⁹ ) groups with one or more heteroatoms to which they are attached: heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl , heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl , where each of these rings in turn is nitro, halogen, cyano, (C ₁ ~C ₆ )-alkyl, halo-(C ₁ –C ₆ )-alkyl, (C ₃ –C ₆ )-cycloalkyl, (C ₃ –C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, ( R ¹⁰ ) ₂ N(O) C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and substituted by m groups of the group consisting of R ¹⁰ O-(C ₁ -C ₆ )-alkyl and oxo;
m represents 0 or 1, 2, 3, 4 or 5,
n represents 0, 1 or 2,
3. A compound of formula (I) according to claim 1 or 2, wherein s represents 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11. A compound of formula (I) according to any one of claims 1 to 3, comprising:
X represents CH ₂ ,
R ¹ represents cyclopropyl, where the cyclopropyl group is substituted by s groups of the group consisting of halogen, (C ₁ -C ₆ )-alkyl and halo-(C ₁ -C ₆ )-alkyl. has been
R ² is hydroxy, (C ₁ -C ₆ )-alkoxy, (C ₁ -C ₆ )-haloalkoxy, (C ₂ -C ₆ )-alkenyloxy, (C ₂ -C ₆ )-haloalkenyloxy, (C ₂ -C ₆ )-alkynyloxy,
or
R ² is (R ⁸ ) ₂ N, R ⁸ (O) C (R ⁸ ) N, R ⁹ O (O) C (R ⁸ ) N, (R ⁸ ) ₂ N (O) C (R ⁸ ) N, R ⁹ (O) ₂ S (R ⁸ ) N, R ⁸ O (O) ₂ S (R ⁸ ) N, (R ⁸ ) ₂ N (O) ₂ S (R ⁸ ) N,
or
Does R ² represent R ⁸ (R ⁸ O)N or
whether R ² represents (R ¹⁷ )(R ¹⁸ )N(R ¹⁹ )N;
or
R ² represents R ¹⁷ R ¹⁸ C=N−(R ¹⁹ )N− ,
R ³ represents cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl,
R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, represents methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl,
R ⁸ is hydrogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-( C ₁ to C ₆ )-alkyl, (C ₃ to C ₆ )-cycloalkyl-(C ₁ to C ₆ )-alkyl-O-(C ₁ to C ₆ )-alkyl, phenyl, phenyl-(C ₁ to C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, represents heteroaryl-O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl, where phenyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl-O-( C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl is respectively nitro, halogen, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl , R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S and R ¹⁰ O−(C ₁ to C ₆ ) - substituted by m groups of the group consisting of alkyl, where the heterocyclyl has n oxo groups,
or
two R ⁸ groups with one or more heteroatoms to which they are attached: heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl, heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclyl forming a ring selected from heteroaryl or heterocyclenylheteroaryl, where each of these rings in turn represents nitro, halogen, cyano, (C ₁ -C ₆ )-alkyl, halo-(C ₁ ~C ₆ )-alkyl, (C ₃ ~C ₆ )-cycloalkyl, (C ₃ ~C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ O－(C ₁ to C ₆ )－ substituted by m groups of the group consisting of alkyl and oxo,
R ⁹ is (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-(C ₁ ~C ₆ )-Alkyl, (C ₃ ~C ₆ )-Cycloalkyl-(C ₁ ~C ₆ )-Alkyl-O-(C ₁ ~C ₆ )-Alkyl, Phenyl, Phenyl-(C ₁ ~C _{6 )} )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl -O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl, where these phenyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl , heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl-O-(C ₁ -C ₆ )-alkyl or heterocyclyl-O-(C ₁ -C ₆ )-alkyl is respectively nitro, halogen, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S and R ¹⁰ O-(C ₁ -C ₆ )-alkyl substituted with m groups of the group consisting of, where the heterocyclyl has n oxo groups,
R ¹⁰ represents hydrogen or (C ₁ -C ₆ )-alkyl,
R ¹¹ represents (C ₁ -C ₆ )-alkyl,
R ¹² represents (C ₁ -C ₄ )-alkyl,
R ¹³ and R ¹⁴ each independently represent hydrogen, (C ₁ -C ₆ )-alkyl, cyano, R ⁸ O(O)C or (R ⁸ ) ₂ N(O)C,
R ¹⁵ and R ¹⁶ each independently represent (C ₁ -C ₆ )-alkyl, phenyl, (C ₃ -C ₆ )-cycloalkyl, heteroaryl or heterocyclyl;
R ¹⁷ , R ¹⁸ and R ¹⁹ are independently R ⁸ or R ⁹ S(O) ₂ , (R ⁸ ) ₂ NS(O) ₂ , R ⁸ OS(O) ₂ , R ⁹ C(O), (R ⁸ ) ₂ NC(O), (R ⁸ ) ₂ NC(S), R ⁸ OC(O), R ⁸ OC(O) C(O), (R ⁸ ) ₂ NC(O) C(O ) or
or (R ¹⁷ and R ¹⁸ ) or (R ¹⁷ and R ¹⁹ ) groups with one or more heteroatoms to which they are attached: heterocyclyl, heterocyclenyl, heteroaryl, arylheterocyclyl, arylheterocyclenyl , heteroarylheterocyclyl, heteroarylheterocyclenyl, heterocyclylheteroaryl or heterocyclenylheteroaryl, where each of these rings in turn represents halogen, cyano, (C ₁ -C ₆ )-Alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, R ¹⁰ O(O)C, (R ¹⁰ ) ₂ N(O)C, R ¹⁰ O, (R ¹⁰ ) ₂ N, R ¹¹ (O) _n S, R ¹⁰ O(O) ₂ S, (R ¹⁰ ) ₂ N(O) ₂ S and R ¹⁰ substituted by m groups of the group consisting of O-(C ₁ -C ₆ )-alkyl and oxo,
m represents 0, 1, 2 or 3,
n represents 0, 1 or 2,
4. A compound of formula (I) according to any one of claims 1 to 3, wherein s represents 0, 1, 2, 3, 4 or 5. A compound of formula (I) according to any one of claims 1 to 4, comprising:
X represents CH ₂ ,
R ¹ represents cyclopropyl, where the cyclopropyl group is substituted by s groups of the group consisting of halogen, (C ₁ -C ₆ )-alkyl and halo-(C ₁ -C ₆ )-alkyl. and
R ² is hydroxy, (C ₁ -C ₆ )-alkoxy, (C ₁ -C ₆ )-haloalkoxy, (C ₂ -C ₆ )-alkenyloxy, (C ₂ -C ₆ )-haloalkenyloxy, (C ₂ - C ₆ )-alkynyloxy,
R ³ represents cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl,
R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently hydrogen, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, represents methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl,
m represents 0, 1, 2 or 3,
n represents 0, 1 or 2,
s represents 0, 1, 2, 3, 4 or 5)
5. A compound of formula (I) according to any one of claims 1 to 4. 6. A herbicidal composition comprising at least one compound of formula (I) according to any one of claims 1 to 5, in admixture with a formulation auxiliary. 7. The herbicidal composition according to claim 6, comprising at least one further insecticidal active substance from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators. Applying an effective amount of at least one compound of formula (I) according to any one of claims 1 to 5 or a herbicidal composition according to claims 6 or 7 to plants or sites of unwanted vegetation. A method for controlling unwanted plants, characterized by: Use of a compound of formula (I) according to any one of claims 1 to 5 or a herbicidal composition according to claims 6 or 7 for controlling unwanted plants. Use according to claim 9 , characterized in that the compound of formula (I) is used for controlling unwanted plants in crops of useful plants. Use according to claim 10, characterized in that the useful plant is a transgenic useful plant.